Cesium carbonate → 3-Bromo-5-cyclopropyl-4-methylpyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,5-dibromo-4-methylpyridine (1.0 g, 0.0039 mol) and cyclopropylboronic acid (0.34 g, 0.0039 mol) in the mixture of 1,4-dioxan (35 mL) and water (15 mL) was added cesium carbonate (2.59 g, 0.00797 mol). Reaction mass was purging with argon for the 20 min. After 20 min, Pd(dppf)2Cl2 (0.14 g, 0.000199 mol) was added. The reaction mixture was heated to 100° C. and stirred for 6 h. The reaction mixture was cooled to room temperature, filtered the reaction mixture through CELITE bed and the CELITE bed was thoroughly washed with ethyl acetate. The filtrate was concentrated under vacuum. The residue was dissolved with dichloromethane and washed with water, saturated aqueous sodium chloride solution, dried over sodium sulphate, concentrated under vacuum, which was purified with silica gel (60-120) column chromatography by 0-2.5% ethyl acetate in hexane to afford the title compound (IN-14). 1H NMR (400 MHz, CdCl3) δ 8.51 (s, 1H), 8.17 (s, 1H), 2.52 (s, 3H), 1.87-1.82 (m, 1H), 1.03-0.99 (m 2H), 0.71-0.68 (m, 2H). MS (M+1): 211.8.

Provenance & Evidence