thiane-4-carbaldehyde

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of tetrahydro-thiopyran-4-carbaldehyde (1.3 g, 9.84 mmol) in DCM (20 mL) was added TMSOTf (3.5 mL, 19.7 mmol) at 0° C. To this mixture 5-Bromo-1H-indole-7-carboxylic acid methyl ester (2.5 g, 9.84 mmol) was added. After 2 hours, Et3SiH (6.2 mL, 39.4 mmol) was added at 0° C., and stirring continued for 18 hours. The reaction mixture was quenched with sodium bicarbone solution and extracted with DCM. The combined organic layers were dried (MgSO4), concentrated, and purified by column chromatography on silica gel, giving 1.6 g (44%) of the title compound. continued for 18 hours The reaction mixture was quenched with sodium bicarbone solution extracted with DCM The combined organic layers were dried (MgSO4) concentrated purified by column chromatography on silica gel

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

Procedure: The title compound was prepared as described in Example 162, Step 1 with 2,6-dibromopyridine (3.64 g, 15.36 mmol) and tetrahydro-2H-thiopyran-4-carbaldehyde (2.00 g, 15.36 mmol) as the starting materials.

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

Procedure: The title compound was prepared according to the procedure in Example 158 Step 1 using 2-bromo-6-methylpyridine (1.5 g, 8.72 mmol) and tetrahydro-2H-thiopyran-4-carbaldehyde (2.27 g, 17.4 mmol) as the starting materials.

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

Procedure: Prepared according to the method of Example 225, Step A, from 2-bromopyridine and tetrahydro-2H-thiopyran-4-carbaldehyde. Prepared

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

Procedure: Tetrahydro-thiopyran-4-carbaldehyde (35.80 g, 275.4 mmol) was added to a solution of compound A2 (80.73 g, 270 mmol) in dichloroethane (700 mL) at −20° C., followed by sodium triacetoxyborohydride (85.84 g, 405 mmol). The mixture was kept at that temperature for 4 h. The solution was diluted with dichloromethane, washed by saturated aqueous sodium bicarbonate, water, brine and dried over anhydrous sodium sulfate The solvent was evaporated and the residue was purified by flash column to yield A3 as a yellow solid (55 g). MS(ESI+) 414.1 (MH+). washed by saturated aqueous sodium bicarbonate, water, brine dried over anhydrous sodium sulfate The solvent was evaporated the residue was purified by flash column

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

Procedure: Tetrahydro-thiopyran-4-carbaldehyde (35.80 g, 275.4 mmol) was added to a solution of compound A2 (80.73 g, 270 mmol) in dichloroethane (700 mL) at −20° C., followed by sodium triacetoxyborohydride (85.84 g, 405 mmol). The mixture was kept at that temperature for 4 h. The solution was diluted with dichloromethane, washed by saturated aqueous sodium bicarbonate, water, brine and dried over anhydrous sodium sulfate The solvent was evaporated and the residue was purified by flash column to yield A3 as a yellow solid (55 g). MS(ESI+) 414.1 (MH+). washed by saturated aqueous sodium bicarbonate, water, brine dried over anhydrous sodium sulfate The solvent was evaporated the residue was purified by flash column

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

Procedure: Tetrahydrothiapyran-4-carboxaldehyde (1.5g) in ethyl acetate (10 ml) was treated with methyl-4-chloroacetoacetate (1.5g), 4A sieve (3g) and the mixture cooled in an ice-bath. Piperidine (3 drops) and acetic acid (3 drops) were now added and the mixture stirred at 0-5° for 45 min. Excess ethyl acetate was added and the organic solution washed with 1M hydrochloric acid. After washing the extracts with water they were dried over anhydrous magnesium sulphate and evaporated to give a colourless oil. Chromatography o silica gel using ethyl acetate-hexane mixtures gave the title compound mixture Z/E (1:2)) as a colourless oil (2g). νmax (CHCl3) 1720 and 1630 cm-1 ; δ(CDCl3) inter alia 3.82(s) and 3.87(s), 6.84 (d, J=10Hz) and 6.94 (d, J™10Hz) m/e 262 (M+). the mixture cooled in an ice-bath the organic solution washed with 1M hydrochloric acid After washing the extracts with water they were dried over anhydrous magnesium sulphate evaporated to give a colourless oil

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

Procedure: To a solution of tetrahydro-thiopyran-4-carbaldehyde (1.3 g, 9.84 mmol) in DCM (20 mL) was added TMSOTf (3.5 mL, 19.7 mmol) at 0° C. To this mixture 5-Bromo-1H-indole-7-carboxylic acid methyl ester (2.5 g, 9.84 mmol) was added. After 2 hours, Et3SiH (6.2 mL, 39.4 mmol) was added at 0° C., and stirring continued for 18 hours. The reaction mixture was quenched with sodium bicarbone solution and extracted with DCM. The combined organic layers were dried (MgSO4), concentrated, and purified by column chromatography on silica gel, giving 1.6 g (44%) of the title compound. continued for 18 hours The reaction mixture was quenched with sodium bicarbone solution extracted with DCM The combined organic layers were dried (MgSO4) concentrated purified by column chromatography on silica gel