Tetrabutylammonium Fluoride → 3-ethynyl-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

Participants

Reaction Steps

To a solution of 4-methyl-N-[4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethylphenyl]-3-trimethylsilanylethynyl-benzamide (2.0 g, 4.1 mmol) in THF (15 mL) was added 5 mL of TBAF in THF (1.0M). After stirring at rt for 1 h, the mixture was partitioned between H2O and EtOAc. The combined organic layers were dried over Na2SO4, filtered, and then concentrated on a rotavap and the residue was purified on a silica gel column (eluent: 10% MeOH in CH2Cl2, MeOH was presaturated with ammonia gas) to give the desired product as a light yellow solid in 78% yield (1.33 g).

Provenance & Evidence