Phenacyl bromide → 2-[2-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridin-1-yl]-1-phenylethanone

HRID 622047

Reaction equation

HRID 622047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:22])[C:10]3[C:11]([N:16]=2)=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 178477971HCID 178477971, compound

Product 1

HCID 143904402-[2-(4-Chlorophenyl)-1H-imidazo[4,5-b]pyridin-1-yl]-1-phenylethanoneYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, the 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (5.0 g, 0.022 mole) was added to a suspension of sodium hydride (0.96 g of 60% in oil, 0.024 mole, washed once with hexanes) in dimethylformamide (100 ml). The mixture was heated at 70°-85° C. for 1.5 hr before adding the α-bromoacetophenone (4.38 g, 0.022 mole) at room temperature. The reaction mixture was stirred at room temperature overnight, then poured into water. The precipitate was collected by filtration, washed with water, and dried under high vacuum. A sample was dissolved in isopropyl alcohol, then concentrated to initiate crystallization. The crystals were collected by filtration, washed with isopropyl alcohol, and dried under high vacuum at 70° C. over a weekend to give 1.5 g (20%) of title compound, mp. 262°-263° C.

Workup

  1. washwashed once with hexanes) in dimethylformamide (100 ml)
  2. temperatureThe mixture was heated at 70°-85° C. for 1.5 hr
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under high vacuum
  6. dissolutionA sample was dissolved in isopropyl alcohol
  7. concentrationconcentrated
  8. customcrystallization
  9. filtrationThe crystals were collected by filtration
  10. washwashed with isopropyl alcohol
  11. customdried under high vacuum at 70° C. over a weekend

Sources & evidence

ORD record
ord-d23849a6a58849eabb710371c112750e
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Linked notes

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