تفاعل #2286389

معادلة التفاعل

methyl-(2-pyridin-3-yl-thiazol-5-yl)-carbamic acid tert-butyl ester

N-bromosuccinimide

→

desired product

المردود 64.3%

(4-bromo-2-pyridin-3-yl-thiazol-5-yl)-methyl-carbamic acid tert-butyl ester

المردود 64.3%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction mixture was concentrated
2. 2
   أخرىthe crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

الإجراء التجريبي

To a solution of methyl-(2-pyridin-3-yl-thiazol-5-yl)-carbamic acid tert-butyl ester (100 mg, 0.34 mmol) in acetonitrile (2 mL) was added N-bromosuccinimide (122 mg, 0.68 mmol) in one portion and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as a white solid (81 mg, 64%): mp 88-91° C.; IR (KBr) 1715 cm−1; 1H NMR (300 MHz, CDCl3) δ 9.11 (s, 1H), 8.70 (d, J=4.2 Hz, 1H), 8.28-8.17 (m, 1H), 7.42 (dd, J=8.1, 4.8 Hz, 1H), 3.27 (s, 3H), 1.48 (s, 9H); ESIMS m/z 372 (M+2).

المصدر