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ChemicalBook CAS DataBase List tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate
946000-13-1

tert-Butyl (4-broMopyridin-2-yl)(Methyl)carbaMate synthesis

8synthesis methods
-

Yield:946000-13-1 76%

Reaction Conditions:

Stage #1: (4-bromopyridin-2-yl)-carbamic acid tert-butyl esterwith sodium hydride in tetrahydrofuran at 0; for 0.25 h;
Stage #2: methyl iodine in tetrahydrofuran at 0 - 20; for 16 h;

Steps:



tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160)To a solution of te/7-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60% dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5% citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO combined organic phases are dried over Na2SO4 and purified by column chromatography (70% EtOAc in heptane) to give the title compound. Yield: 240 mg (76%). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).

References:

WO2008/57497,2008,A2 Location in patent:Page/Page column 296-297