Acetic Acid → 1,1-Dimethylethyl N-(5-bromo-1,2-dihydro-1-methyl-2-oxo-3-pyridinyl)-N-[5-[(ethylamino)methyl]-2-pyridinyl]carbamate

Participants

Reaction Steps

(5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (500 mg, 1.22 mmol), ethanamine (6.12 ml of a 2.0 M solution in THF), sodium triacetoxyborohydride (649 mg, 3.06 mmol), and acetic acid (147 mg, 2.45 mmol) were added to a 20 ml microwave vial. The vial was capped and heated in a sand bath at 40 degrees centigrade overnight. TLC and LCMS analysis showed the reaction to be incomplete. Another 6 ml of ethanamine was added to the vial and the reaction was heated again at 40 degrees centigrade overnight. The reaction was diluted with DCM and washed with saturated aqueous sodium bicarbonate, dried and concentrated. The crude product was purified by flash chromatography using 10% methanol in DCM to give 340 mg (63.5%) of (5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-(5-ethylaminomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester.

Provenance & Evidence