Triethylamine → HCID 89421807, compound

Participants

Reaction Steps

To solution of 1-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)butan-1-one (6.62 g, 18.41 mmol) in DCM (35 mL) was added 2,4-dimethoxybenzylamine (3.20 mL, 21.30 mmol) and NEt3 (7.0 mL, 50.22 mmol). Mixture was cooled to 0° C. before TiCl4 solution (1M DCM, 12.0 mL, 12.0 mmol) was added dropwise via syringe pump over 30 min. Reaction was allowed to warm to room temperature and stirred overnight. Mixture was diluted with DCM (100 mL) and then quenched with NaHCO3 (aqueous saturated, ˜30 mL). Upon vigorous shaking organic phase was separated using PTFE phase separator and dried over Na2SO4. Removal of the solvent afforded N-(1-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)butylidene)-1-(2,4-dimethoxyphenyl)methanamine as yellow oil, which was taken directly into next step without purification.

Provenance & Evidence