Dimethylformamide → Tert-butyl 4-formylpyridin-3-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyllithium (1.7 M, 14.5 mL, 24.6 mmol, 2.39 equiv) was added to a solution of pyridin-3-yl-carbamic acid tert-butyl ester (6-1, 4.00 g, 20.6 mmol, 1 equiv) in THF (100 mL) at −78° C., and the resulting mixture stirred for 1 h. N,N-dimethylformamide (8.00 mL, 103 mmol, 5 equiv) was added, and the reaction mixture was warmed to 0° C. and stirred for 30 min. The mixture was partitioned between water (400 mL) and ethyl acetate (3×150 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (20% ethyl acetate in hexanes, grading to 40% ethyl acetate in hexanes) to afford (4-formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (6-2) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 10.00 (s, 1H), 9.89 (br s, 1H), 9.84 (s, 1H), 8.53 (d, 1H, J=4.8 Hz), 7.49 (d, 1H, J=4.8 Hz), 1.55 (s, 9H); TLC (EtOAc), Rf=0.47.

Provenance & Evidence