Benzoyl chloride → HCID 11370144, compound

Participants

Reaction Conditions

Reaction Steps

3-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]pyridine 1-oxide (2-1, 0.156 g, 01.53 mmol) in anhydrous CH3CN (10.0 mL) was treated with benzoyl chloride (0.073 mL, 0.089 mmol) and triethylamine (0.088 mL, 0.636 mmol) and the mixture was cooled to 0° C. Trimethylsilyl cyanide (0.136 mL, 1.06 mmol) was added and the reaction stirred 48 h at 25° C. The reaction was directly subjected to flash chromatography (SiO2, ISCO 10 g Redi-sep, 1% EtOAc/CH2Cl2) followed by preparative TLC (100% CH2Cl2) and provided 5-[2-(1-phenylcyclopropyl)-1,3-thiazol-4-yl]pyridine-2-carbonitrile (2-2). 1H NMR (300 MHz, CDCl3) δ 9.82 (d, J=1.5 Hz, 1H), 8.31 (dd, J=8.2, 2.2 Hz, 1H), 7.72 (dd, J=8.2, 0.7 Hz, 1H), 7.52 (m, 2H), 7.47 (s, 1H), 7.40 (m, 3H), 1.86 (dd, J=6.9, 3.9 Hz, 2H), 1.50 (dd, J=6.9, 3.9 Hz, 2H); MS 304.0 found 304.4 (M+H+) required.

Provenance & Evidence