N-(4-Bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-5-nitro-nicotinamide → 5-amino-N-(4-bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-nicotinamide

HRID 2042810Notes

Reaction equation

HRID 2042810 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[C:13]([NH:19][CH3:20])=[N:12][C:11]=2[O:21][CH2:22][CH:23]([F:25])[F:24])=[CH:4][CH:3]=1>[Ni].C1COCC1>[NH2:16][C:14]1[C:13]([NH:19][CH3:20])=[N:12][C:11]([O:21][CH2:22][CH:23]([F:25])[F:24])=[C:10]([CH:15]=1)[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:26]

Participants

4

Reactant 1

HCID 86664893N-(4-Bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-5-nitro-nicotinamide

Product 1

HCID 866648925-amino-N-(4-bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-nicotinamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-bromo-phenyl)-2-(2,2-difluoro-ethoxy)-6-methylamino-5-nitro-nicotinamide (150 mg, 0.35 mmol), THF (10 mL) and Ra—Ni (15 mg) is stirred for 6 h at rt under a hydrogen atmosphere (3.0 bar). The catalyst is removed by filtration and the filtrate is concentrated to give the sub-title compound.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-c009d939a2574362ae9ed5a9e4112676
Source dataset
uspto-grants-2013_11
Patent number
US08586604B2

Reaction notes

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