N-methoxy-N-methyl-2-(thiophen-2-yl)acetamide → 1-[4-(1-Azido-1-methylethyl)phenyl]-2-(2-thienyl)ethanone

반응식

[Li]CCCC.[N:6]([C:9]([C:12]1[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=[N+:7]=[N-:8].CON(C)[C:22](=[O:29])[CH2:23][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>C1COCC1>[N:6]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:22](=[O:29])[CH2:23][C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=[N+:7]=[N-:8]

참가 물질

실험 절차

nBuLi (1.6M in hexane, 2.88 mL, 4.60 mmol) was added dropwise to a solution of 1-(1-azido-1-methylethyl)-4-bromobenzene (2-3, 1.03 g, 4.28 mmol) in THF (20 mL) at −78° C. After 15 min a solution of N-methoxy-N-methyl-2-thien-2-ylacetamide (1-1, 0.78 g, 4.18 mmol) in THF (1 mL) was added. After an additional 30 min at −78° C., the reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate, dried over magnesium sulfate, filtered, and concentrated to give an oil. The crude product was purified via automated flash column chromatography on silica gel (5% CH2Cl2, 0-10% EtOAc/hexanes over 30 min) to give the title compounds as a yellow oil. LRMS m/z (M+1) Calcd: 286.1,. Found 286.2.