2,6-dimethylthian-4-one

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.0 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound. dried flask containing 3 Å molecular sieves added to the reaction via syringe pump over 2 hours after which it was stirred for 3 hours between 0 and 10° C The reaction was cooled to 0° C. was stirred at room temperature overnight The reaction was then quenched with a saturated sodium bicarbonate solution filtered extracted with DCM The combined organics were washed with water The combined aqueous layers were back-extracted with DCM The combined organics were washed with brine dried with MgSO4 concentrated The crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound. added to the solution above and extracted with diethyl ether The combined organics were washed with brine, dried MgSO4 concentrated The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.03 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound. dried flask containing 3 Å molecular sieves added to the reaction via syringe pump over 2 hours after which it was stirred for 3 hours between 0 and 10° C The reaction was cooled to 0° C. was stirred at room temperature overnight The reaction was then quenched with a saturated sodium bicarbonate solution filtered extracted with DCM The combined organics were washed with water The combined aqueous layers were back-extracted with DCM The combined organics were washed with brine dried with MgSO4 concentrated The crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.03 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound. dried flask containing 3 Å molecular sieves added to the reaction via syringe pump over 2 hours after which it was stirred for 3 hours between 0 and 10° C The reaction was cooled to 0° C. was stirred at room temperature overnight The reaction was then quenched with a saturated sodium bicarbonate solution filtered extracted with DCM The combined organics were washed with water The combined aqueous layers were back-extracted with DCM The combined organics were washed with brine dried with MgSO4 concentrated The crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound. added to the solution above and extracted with diethyl ether The combined organics were washed with brine, dried MgSO4 concentrated The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.0 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound. dried flask containing 3 Å molecular sieves added to the reaction via syringe pump over 2 hours after which it was stirred for 3 hours between 0 and 10° C The reaction was cooled to 0° C. was stirred at room temperature overnight The reaction was then quenched with a saturated sodium bicarbonate solution filtered extracted with DCM The combined organics were washed with water The combined aqueous layers were back-extracted with DCM The combined organics were washed with brine dried with MgSO4 concentrated The crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound. added to the solution above and extracted with diethyl ether The combined organics were washed with brine, dried MgSO4 concentrated The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound. added to the solution above and extracted with diethyl ether The combined organics were washed with brine, dried MgSO4 concentrated The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.03 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound. dried flask containing 3 Å molecular sieves added to the reaction via syringe pump over 2 hours after which it was stirred for 3 hours between 0 and 10° C The reaction was cooled to 0° C. was stirred at room temperature overnight The reaction was then quenched with a saturated sodium bicarbonate solution filtered extracted with DCM The combined organics were washed with water The combined aqueous layers were back-extracted with DCM The combined organics were washed with brine dried with MgSO4 concentrated The crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound. added to the solution above and extracted with diethyl ether The combined organics were washed with brine, dried MgSO4 concentrated The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,6-Dimethyltetrahydro-4H-thiopyran-4-one (0.293 g, 2.03 mmol) was dissolved in dichloromethane (35 mL) in an oven dried flask containing 3 Å molecular sieves and stirred under argon at 0° C. TMS-OTf (0.451 g, 2.0 mmol, 0.36 mL) was added slowly to the mixture over 10 min. Ethyl 5-bromo-1H-indole-7-carboxylate (0.293 g, 2.031 mmol) was dissolved in DCM (10 mL) and added to the reaction via syringe pump over 2 hours, after which it was stirred for 3 hours between 0 and 10° C. The reaction was cooled to 0° C. and triethylsilane (0.353 g, 0.485 mL, 3.04 mmol) was then added all at once and the reaction was stirred at room temperature overnight. The reaction was then quenched with a saturated sodium bicarbonate solution, filtered, then extracted with DCM. The combined organics were washed with water. The combined aqueous layers were back-extracted with DCM. The combined organics were washed with brine, dried with MgSO4, and concentrated. The crude compound was purified on Combiflash silica column with 0-30% EA/DCM to give 0.212 g (26%) of the title compound. dried flask containing 3 Å molecular sieves added to the reaction via syringe pump over 2 hours after which it was stirred for 3 hours between 0 and 10° C The reaction was cooled to 0° C. was stirred at room temperature overnight The reaction was then quenched with a saturated sodium bicarbonate solution filtered extracted with DCM The combined organics were washed with water The combined aqueous layers were back-extracted with DCM The combined organics were washed with brine dried with MgSO4 concentrated The crude compound was purified on Combiflash silica column with 0-30% EA/DCM

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,6-Heptadien-4-one (0.50 g, 4.54 mmol) was dissolved in toluene (8 mL) and water (4 mL). Sodium sulfide nonahydrate (1.09 g, 4.54 mmol) was dissolved in water (4 mL) and added to the solution above and stirred at room temp. After 5 h, the aqueous layer was saturated with potassium carbonate and extracted with diethyl ether. The combined organics were washed with brine, dried MgSO4, and concentrated. The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes to give 0.193 g (29%) of the title compound. added to the solution above and extracted with diethyl ether The combined organics were washed with brine, dried MgSO4 concentrated The crude compound was purified on a Combiflash silica column with 0-10% EtOAc/hexanes