N-bromobutanimide → 3-Bromo-5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amine

HRID 1710688Notes

Reaction equation

HRID 1710688 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[CH:10][C:11]([NH2:20])=[N:12][C:13]=1[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[Br:21]N1C(=O)CCC1=O>CS(C)=O.O>[Br:21][C:10]1[C:11]([NH2:20])=[N:12][C:13]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[C:8]([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[F:1])[N:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 160708355-(3-Fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amine

Product 1

HCID 594576503-Bromo-5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amineYield 31%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a 0° C. stirred solution of 5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyrazin-2-amine (Example 115) (1.10 g, 4.11 mmol) in a mixture of DMSO (13 mL) and water (0.34 mL), was added N-bromosuccinimide (0.77 g, 4.32 mmol) in portions. After stirring for 5 h at room temperature, the mixture was poured into water, the precipitate collected by filtration, washed with water and dried to give the title compound as a green solid (0.44 g, 31%).

Workup

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

Sources & evidence

ORD record
ord-0dc508299fd24ca8836ea461e1c9a048
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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