Methanol → 2-(5-Methoxy-7-methyl-1H-indol-4-yl)acetonitrile

Participants

Reaction Steps

To a suspension of KOtBu (6.98 g, 62.2 mmol) in THF (50.0 mL) at −78° C. was added TOSMIC (8.10 g, 41.5 mmol) in THF (50.0 mL). The mixture was stirred at −78° for 15 minutes. To the mixture at −78° C. was then added a solution of tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (6 g, 20.74 mmol) in THF (50 mL). The reaction was stirred at −78° C. for 1.5 hours. MeOH (10 ml) was then added and the reaction was removed from the dry ice bath. After 30 minutes the reaction was placed in a 40° C. water bath for 30 minutes. At this point, the reaction was cooled in an ice bath and was quenched with a saturated solution of ammonium chloride and then diluted with water and EtOAc. The layers were separated and the organics layer was dried, concentrated and absorbed onto silica to purify via FCC (0-50% EtOAc:heptanes) to afford the title compound. MS (ESI+) m/z 201.2 (M+H).

Provenance & Evidence