Allyl bromide → Allyl-(4-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (4-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (6.78 g, 29.7 mmol), allyl bromide (5.1 g, 40.8 mmol) and cesium carbonate (20.1 g, 61.8 mmol) in DMF (200 mL) is heated at 60° C. for 1 h. The reaction is quenched with water, extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography eluting with 0-40% EtOAc in heptane to afford allyl-(4-chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (5.66 g, 71%). MS: 269 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.42(d, 1H), 7.40 (d, 1H), 5.80-5.98 (m, 1H), 4.35-4.51 (m, 1H), 3.90-4.07 (m, 1H).

Provenance & Evidence