Tert-Butyl nitrite → HCID 59274099、化合物

反応式

[CH2:1]([C:8]1[CH:9]=[C:10]([Br:15])[C:11](N)=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=[O:17]>CN(C=O)C.O>[CH2:1]([C:8]1[CH:9]=[C:10]([Br:15])[C:11](=[O:17])[NH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

実験手順

To a stirred solution of 5-benzyl-3-bromopyridin-2-amine 3 (0.2 g, 0.7 mmol) in DMF (4 mL) was added water (2 drops) followed by t-butyl nitrite (0.378 g, 3.6 mmol) and the reaction mixture stirred at RT for 30 min. DMF and the excess reagent were distilled off, and the residue purified by flash chromatography on silica gel (EtOAc:hexane, 1:1). Yield 7.3 g (86%), white solid, mp 151-152° C. 1H NMR (CDCl3, 500 MHz): δ 3.77 (s, 2H, CH2), 7.17-7.36 (m, 6H, Ar—H and CH), 7.76 (d, 1H, CH, J=1.5 Hz) 13.25 (bs, 1H, NH). 13C NMR (CDCl3, 125 MHz): δ 37.3, 115.4, 121.0, 126.9, 128.8, 128.8, 128.9, 128.9, 132.4, 138.5, 145.3, 161.0; HRMS (M+H)+ calcd for C12H11BrNO 264.0024, found 264.0014.