6-chloro-2-methyl-1H-indole

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

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

Procedure: To a solution of 2-chloroethylmorpholine HCl (134 mg, 0.72 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 6-chloro-2-methylindole (100 mg, 0.60 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between H2O and toluene, and the organic extract washed two times with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 50% ethyl acetate in hexane to give a final yield of 149 mg (0.54 mmol). 1H NMR (500 MHz, CDCl3, δ): 2.44 (s, 3H), 2.49 (t, J=4.4 Hz, 4H), 2.62 (t, J=7.2 Hz, 2H), 3.73 (t, J=4.5 Hz, 4H), 4.11 (t, J=7.2 Hz, 2H), 6.23 (s, 1H), 7.06 (dd, J=8.4 Hz, 1.7 Hz, 1H), 7.28 (s, 1H), 7.42 (d, J=8.3 Hz, 1H). 13C NMR (500 MHz, CDCl3, δ): 12.79, 41.18, 54.11, 57.83, 67.5, 100.30, 108.95, 119.90, 120.53, 126.40, 126.70, 137.06, 137.37. MS m/z 279.3 [M+H]+. stirred overnight The reaction mixture was partitioned between H2O and toluene the organic extract washed two times with H2O dried over MgSO4 filtered concentrated in vacuo The crude product was purified via silica gel chromatography to give a final yield of 149 mg (0.54 mmol)

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

Procedure: To a solution of 2-chloroethylmorpholine HCl (134 mg, 0.72 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 6-chloro-2-methylindole (100 mg, 0.60 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between H2O and toluene, and the organic extract washed two times with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 50% ethyl acetate in hexane to give a final yield of 149 mg (0.54 mmol). 1H NMR (500 MHz, CDCl3, δ): 2.44 (s, 3H), 2.49 (t, J=4.4 Hz, 4H), 2.62 (t, J=7.2 Hz, 2H), 3.73 (t, J=4.5 Hz, 4H), 4.11 (t, J=7.2 Hz, 2H), 6.23 (s, 1H), 7.06 (dd, J=8.4 Hz, 1.7 Hz, 1H), 7.28 (s, 1H), 7.42 (d, J=8.3 Hz, 1H). 13C NMR (500 MHz, CDCl3, δ): 12.79, 41.18, 54.11, 57.83, 67.5, 100.30, 108.95, 119.90, 120.53, 126.40, 126.70, 137.06, 137.37. MS m/z 279.3 [M+H]+. stirred overnight The reaction mixture was partitioned between H2O and toluene the organic extract washed two times with H2O dried over MgSO4 filtered concentrated in vacuo The crude product was purified via silica gel chromatography to give a final yield of 149 mg (0.54 mmol)

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)

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

Procedure: To a solution of 2-chloroethylmorpholine HCl (134 mg, 0.72 mmol) in 0.3 mL DMSO was added pulverized KOH (102 mg, 1.81 mmol), then after 10 min, a solution of 6-chloro-2-methylindole (100 mg, 0.60 mmol) in 0.2 mL DMSO was added and the reaction stirred at room temperature overnight. Additional 2-chloroethylmorpholine (22 mg, 0.12 mmol) and KOH (17 mg, 0.3 mmol) added and stirred overnight. The reaction mixture was partitioned between H2O and toluene, and the organic extract washed two times with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified via silica gel chromatography using a gradient from 0 to 50% ethyl acetate in hexane to give a final yield of 149 mg (0.54 mmol). 1H NMR (500 MHz, CDCl3, δ): 2.44 (s, 3H), 2.49 (t, J=4.4 Hz, 4H), 2.62 (t, J=7.2 Hz, 2H), 3.73 (t, J=4.5 Hz, 4H), 4.11 (t, J=7.2 Hz, 2H), 6.23 (s, 1H), 7.06 (dd, J=8.4 Hz, 1.7 Hz, 1H), 7.28 (s, 1H), 7.42 (d, J=8.3 Hz, 1H). 13C NMR (500 MHz, CDCl3, δ): 12.79, 41.18, 54.11, 57.83, 67.5, 100.30, 108.95, 119.90, 120.53, 126.40, 126.70, 137.06, 137.37. MS m/z 279.3 [M+H]+. stirred overnight The reaction mixture was partitioned between H2O and toluene the organic extract washed two times with H2O dried over MgSO4 filtered concentrated in vacuo The crude product was purified via silica gel chromatography to give a final yield of 149 mg (0.54 mmol)

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

Procedure: A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1,2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. After 5 min, the reaction mixture was cooled to room temperature and quenched with water. The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%). The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate) to give the title compound (0.39 g; 27%) as a white solid. quenched with water The pH was adjusted to 14 by the addition of aqueous sodium hydroxide solution (32%) The aqueous layer was extracted with tert-butyl methyl ether (3×200 ml) The combined organic layers were dried over sodium sulfate concentrated in vacuo The residue was purified by flash-chromatography (aminopropyl-modified silica gel, n-heptane/ethyl acetate)