Dimethylformamide → 4-Methyl-5-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)thiazole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-methyl-5-(spiro[indene-1,4′-piperidine]-1′-ylmethyl) thiazole (3.8 g, 10.12 mmol) in THF is added n-BuLi (0.713 g, 11.13 mmol) at −78° C. The mixture is warmed to −45° C. and stirred for 30 minutes. DMF (1.5 mL) is added dropwise to the mixture at −78° C. and the mixture is slowly warmed to room temperature and stirred for an hour. The mixture is cooled to −78° C., diluted with water, followed by NH4Cl solution. The mixture is extracted with ethyl acetate, dried over Na2SO4, and evaporated to dryness to give the title compound (2.8 g, 85%). ESI/MS m/z 325 (M+H)+.

Provenance & Evidence