Propionitrile → 2-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine

HRID 918782Notes

Reaction equation

HRID 918782 reaction equation
Br.C(O[CH2:6][CH2:7][N:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]1=[NH:18])(=O)C.P(Br)(Br)([Br:21])=O.C(#N)CC.C(=O)(O)[O-].[Na+]>>[Br:21][C:6]1[N:18]=[C:9]2[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][N:8]2[CH:7]=1

Participants

5

Reactant 4

HCID 7854PropionitrileHCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 118020257HCID 118020257, compound

Product 1

HCID 401480152-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridineYield 61.6%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.63 g of (2-imino-5-trifluoromethyl-2H-pyridin-1-yl)ethyl acetate hydrobromide, 2.84 g of phosphorus oxybromide and 2 ml of propionitrile was stirred at 100° C. for 2.5 hours. The cooled reaction mixture was neutralized in a saturated aqueous sodium bicarbonate solution and a 5 M aqueous sodium hydroxide solution, and the precipitated solid was filtered. The resulting solid was washed with water and n-hexane to obtain 808 mg of 2-bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine.

Workup

  1. customThe cooled reaction mixture
  2. filtrationa 5 M aqueous sodium hydroxide solution, and the precipitated solid was filtered
  3. washThe resulting solid was washed with water and n-hexane

Sources & evidence

ORD record
ord-91d1c8a397ac46538594b552431e13fc
Source dataset
uspto-grants-2016_03
Patent number
US09271500B2

Reaction notes

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