Tert-Butyl nitrite → HCID 59274099, compound

HRID 1364371Notes

Reaction equation

HRID 1364371 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

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 14761929HCID 14761929, compound

Product 1

HCID 59274099HCID 59274099, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

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.

Workup

  1. distillationDMF and the excess reagent were distilled off
  2. customthe residue purified by flash chromatography on silica gel (EtOAc:hexane, 1:1)

Sources & evidence

ORD record
ord-054ceac76d434846abf5f9c344522490
Source dataset
uspto-grants-2011_02
Patent number
US07888375B2

Reaction notes

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