N-bromobutanimide → 5-bromo-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine

HRID 253975Notes

Reaction equation

HRID 253975 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[C:18]1[C:19]([NH2:24])=[N:20][CH:21]=[CH:22][CH:23]=1.[Br:25]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(#N)C>[Br:25][C:22]1[CH:23]=[C:18]([C:10]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[C:17]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:11]=2)[C:19]([NH2:24])=[N:20][CH:21]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 581795463-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine

Product 1

HCID 581800415-bromo-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amineYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (2.4 g, 7.43 mmol) in acetonitrile (70 mL) was treated with N-bromosuccinimide (1.45 g, 18.17 mmol) at 0° C. and the reaction mixture stirred for 30 min. reaction mixture was treated with saturated aq. NaHCO3 solution (150 mL), stirred for 30 min, and the resulting precipitate filtered and dissolved in CHCl3 (200 mL). The combined organics were washed with water (3×70 mL), brine (70 mL), and dried (Na2SO4). Filtration and evaporation of solvent in vacuo gave a solid, which was purified by silica gel chromatography (4% methanol/chloroform) to give 5-bromo-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (2.2 g, 75% yield) as a light yellow solid; LC-MS: 402.0, 404.0 (M+H).

Workup

  1. customreaction mixture
  2. stirringstirred for 30 min
  3. filtrationthe resulting precipitate filtered
  4. dissolutiondissolved in CHCl3 (200 mL)
  5. washThe combined organics were washed with water (3×70 mL), brine (70 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and evaporation of solvent in vacuo
  8. customgave a solid, which
  9. customwas purified by silica gel chromatography (4% methanol/chloroform)

Sources & evidence

ORD record
ord-6e4546804f284966847e8acaf4df9a45
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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