6-fluoro-5-phenylmethoxy-1H-indole

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

Procedure: To a stirred solution of 5-benzyloxy-6-fluoroindole (Intermediate 26, 2.0 g, 8.3 mmol) in dry DMF (30 mL) was sodium hydride (60% in mineral oil, 0.35 g, 8.7 mmol) added at 0° C. The solution was stirred for 30 minutes at room temperature and the reaction mixture was cooled to 0° C. and benzenesulfonyl chloride (1.17 mL, 9.12 mmol) was added dropwise. The reaction mixture was kept at 4° C. overnight, and a drop of methanol was added and the solvent was evaporated. The crude material was dissolved in DCM, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and evaporated. The crude material was purified by flash chromatography on silica gel using DCM as the eluent to give the title compound (2.88 g) as a light yellow oil. MS m/z 382 [M+H]+. added at 0° C the reaction mixture was cooled to 0° C. The reaction mixture was kept at 4° C. overnight the solvent was evaporated The crude material was dissolved in DCM washed with saturated aqueous NaHCO3 dried over MgSO4 filtered evaporated The crude material was purified by flash chromatography on silica gel

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

Procedure: To a stirred solution of 5-benzyloxy-6-fluoroindole (Intermediate 26, 2.0 g, 8.3 mmol) in dry DMF (30 mL) was sodium hydride (60% in mineral oil, 0.35 g, 8.7 mmol) added at 0° C. The solution was stirred for 30 minutes at room temperature and the reaction mixture was cooled to 0° C. and benzenesulfonyl chloride (1.17 mL, 9.12 mmol) was added dropwise. The reaction mixture was kept at 4° C. overnight, and a drop of methanol was added and the solvent was evaporated. The crude material was dissolved in DCM, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and evaporated. The crude material was purified by flash chromatography on silica gel using DCM as the eluent to give the title compound (2.88 g) as a light yellow oil. MS m/z 382 [M+H]+. added at 0° C the reaction mixture was cooled to 0° C. The reaction mixture was kept at 4° C. overnight the solvent was evaporated The crude material was dissolved in DCM washed with saturated aqueous NaHCO3 dried over MgSO4 filtered evaporated The crude material was purified by flash chromatography on silica gel