N-bromobutanimide → (5-Bromopyrazin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

HRID 1404276Notes

Reaction equation

HRID 1404276 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:9]=[N:10][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:13]=1.[Br:18]N1C(=O)CCC1=O>CO>[Br:18][C:5]1[N:4]=[CH:3][C:2]([NH:7][C:8]2[CH:9]=[N:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)=[N:1][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66615925Pyrazin-2-yl-(6-trifluoromethyl-pyridin-3-yl)-amine

Product 1

HCID 86634697(5-Bromopyrazin-2-yl)-(6-trifluoromethyl-pyridin-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of pyrazin-2-yl-(6-trifluoromethyl-pyridin-3-yl)-amine (0.47 g) was dissolved in 50 Ml MeOH and then charged with N-bromosuccinimide (0.35 g) in a single portion as a solid. The reaction was stirred overnight at room temperature, then concentrated in vacuo. Purification by silica gel chromatography (25% EtOAc in hexanes) afforded the title compound: 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 6.7 (s, 1 H) 7.5 (s, 1 H) 7.9 (s, 1 H) 8.2 (s, 2 H) 8.6 (s, 1 H); (M+H)+ 320.9.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by silica gel chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-266096dffdea461aaa9466a5ef2d7470
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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