Isopropylamine → 4-Chloro-N-isopropyl-pyridine-2-carboxamide

Participants

Reaction Steps

A 0° C. solution of isopropylamine (0.971 mL, 11.30 mmol) and DIEA (1.973 mL, 11.30 mmol) in MeOH (10 mL) and THF (5 mL) was treated with 4-chloropicolinoyl chloride hydrochloride (0.8 g, 3.77 mmol) in one portion, warmed to RT and stirred for 2 h. The mixture was diluted with EtOAc, washed with satd. NaHCO3, then brine and the organic layer was dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (EtOAc/Hex) to afford 4-chloro-N-isopropylpicolinamide (0.67 g, 90%). 1H NMR (400 MHz, DMSO-d6): δ 8.60 (d, J=5.3 Hz, 1H), 8.56 (d, J=8.4 Hz, 1H), 8.00 (d, J=2.2 Hz, 1H), 7.75 (dd, J=5.3, 2.1 Hz, 1H), 4.10-4.09 (m, 1H), 1.17 (d, J=6.6 Hz, 6H); MS (ESI) m/z: 199.1 (M+H+).

Provenance & Evidence