Hydrochloric Acid → HCID 57808404, compound

Participants

Reaction Steps

To a solution of 2-chloro-pyridine-4-carboxylic acid (2.55 g, 16.2 mmol) in dioxane (50 mL), Pd(dppf) (132 mg, 0.162 mmol) is added. The mixture is stirred under argon at rt and isobutyl zinbromide (6.55 g, 32.4 mmol, 65 mL of a 0.5 M solution in THF) is added dropwise. The mixture is stirred at rt for 1 h, then at 100° C. for 16 h. The mixture is cooled to rt and diluted with EA (250 mL) and cold water (0° C.). The mixture is acidified by adding aq. 25% HCl. The org. phase is separated and the aq. phase is extracted with EA (4×50 mL) followed by DCM (6×50 mL). The combined org. extracts are concentrated and dried. The crude product is purified by MPLC on silica gel to give the title compound (2.0 g) in form of a pale yellow oil. LC-MS: tR=0.47 min, [M+1]+=180.09. 1H NMR (CD3OD): δ 1.03 (d, J=6.8 Hz, 6H), 2.12-2.24 (m, 1H), 3.00 (d, J=7.3 Hz, 2H), 8.29 (dd, J=5.8, 1.5 Hz, 1H), 8.34 (s, 1H), 8.88 (d, J=5.8 Hz, 1H).

Provenance & Evidence