Diisopropylethylamine → 4-Chloro-2-[(6-trifluoromethyl-pyridin-3-ylmethyl)-amino]-thiazole-5-carbaldehyde

Participants

Reaction Steps

To a solution of C-(6-trifluoromethyl-pyridin-3-yl)-methylamine (74, 1.0 g, 5.7 mmol) and N,N-diisopropylethylamine (2.0 mL, 11 mmol) in 100 mL of tetrahydrofuran, 2,4-dichloro-thiazole-5-carbaldehyde (73, 1.1 g, 6.2 mmol) in 10 mL of tetrahydrofuran was added dropwise at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (75, 1.2 g, 66%). MS (ESI)=[M+H+]+=322.11

Provenance & Evidence