Ammonia → 2-Bromoimidazo[1,2-a]pyridine

HRID 2051111Notes

Reaction equation

HRID 2051111 reaction equation
P(Br)(Br)([Br:3])=O.O[C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[CH:15]=1.N>>[Br:3][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[CH:15]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24613Phosphorus oxybromideHCID 14674030Imidazo[1,2-a]pyridin-2-ol

Product 1

HCID 124289572-Bromoimidazo[1,2-a]pyridineYield 19.9%

Conditions

Temperature
90 °C

Procedure

To 44.0 g of melted phosphorus oxybromide, 12.0 g of 2-hydroxyimidazo[1,2-a]pyridine is added at 60°-85° C. and stirred for 3 hours at 90° C. The mixture is poured into 300 ml of ice water, neutralized with aqueous ammonia and then extracted with chloroform. The collected chloroform layer is dried over anhydrous sodium sulfate. Chloroform is distilled off and the residue is purified by silica gel chromatography (eluent: chloroform) to obtain 3.5 g of the title compound as a crystalline solid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe collected chloroform layer is dried over anhydrous sodium sulfate
  3. distillationChloroform is distilled off
  4. customthe residue is purified by silica gel chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-3b91fc7bc6524740bf49fea0aaeb9b01
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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