Tert-Butyl nitrite → HCID 59274099, compound

Reaction equation

[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

Participants

Procedure

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.