N-bromobutanimide → 5-Bromo-6-(3-fluorophenyl)pyrazin-2-amine

HRID 1710677Notes

Reaction equation

HRID 1710677 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([NH2:14])[CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:15]N1C(=O)CCC1=O>CS(C)=O.O>[Br:15][C:9]1[N:10]=[CH:11][C:12]([NH2:14])=[N:13][C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 457883426-(3-Fluorophenyl)pyrazin-2-amine

Product 1

HCID 594576145-Bromo-6-(3-fluorophenyl)pyrazin-2-amineYield 85%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a 0° C. cooled stirred solution of 6-(3-fluorophenyl)pyrazin-2-ylamine (0.5 g, 2.64 mmol) in a mixture of DMSO (10 mL) and water (0.25 mL), was added N-bromosuccinimide (0.518 g, 2.90 mmol) in portions. After stirring for 5 h, the mixture was poured into water, the precipitate collected by filtration, washed with water and dried to give the title compound as a yellow solid (0.60 g, 85%).

Workup

  1. filtrationthe precipitate collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-95c2028c50c24acd974485b65098c019
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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