Ammonium Chloride → HCID 53909268, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (18.25 mmole) was added dropwise to a cooled solution of 6-bromo-2-methoxypyridine (3.12 g, 16.6 mmole, prepared from 2,6-dibromopyridine (Aldrich) according to Comins and Killpack, J. Org. Chem., 55:69-73 (1990)) in 40 mL of THF at -78° C., the resulting orange solution was stirred for 20 minutes at -78° C., and t-butylisocyanate (26.3 mmole) was added with a syringe. The mixture was stirred for 30 minutes at -78° C., warmed to room temperature, then saturated NH4Cl (20 mL) was added. The layers were separated, and the aqueous layer was extracted with methylene chloride (2×20 mL). The combined organic layers were dried over MgSO4 and concentrated, and the residue was chromatographed on silica gel, eluting with 10% to 25% ethyl acetate in hexane, to provide 2.93 g of the title compound as an oil. MS: 209 (M+H)+ ; 1H NMR (CDCl3) δ: 7.85-7.68 (m, 3H), 6.87 (d, J=8 Hz, 1H), 3.96 (s, 3H), 1.49 (s, 9H).

Provenance & Evidence