Acetonitrile → 8-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1801761Notes

Reaction equation

HRID 1801761 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH2:12]1[C:17](=O)N(Br)[C:14](=O)[CH2:13]1.[C:20]([O-:23])(O)=[O:21].[Na+].[C:25](#N)[CH3:26]>>[F:11][C:2]([F:1])([F:10])[C:3]1[C:4]2[N:5]([C:25]([C:20]([OH:23])=[O:21])=[CH:26][N:9]=2)[CH:6]=[C:7]([C:12]2[CH:17]=[CH:8][C:3]([C:2]([F:11])([F:10])[F:1])=[CH:14][CH:13]=2)[CH:8]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 27609202-Amino-3-(trifluoromethyl)pyridine

Product 1

HCID 866116268-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acidYield 98%

Conditions

Temperature
23 °C

Procedure

To a solution of the above 3-trifluoromethyl-pyridin-2-ylamine (16.21 g, 100 mmol) in acetonitrile (300 mL) at 5° C. was added NBS (17.8 g, 100 mmol) and the mixture was stirred at 23° C. for 1 h. Poured into ice and additional sat. NaHCO3-sol., extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a yellow solid, which was filtered through a silica gel and cotton wool column with dichloromethane to give the title compound as a yellow solid (23.71 g, 98%). MS (EI) 240.1 [(M)+], 242.0 [(M+2)+].

Workup

  1. extraction, extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customRemoval of the solvent in vacuum
  5. waitleft a yellow solid, which
  6. filtrationwas filtered through a silica gel and cotton wool column with dichloromethane

Sources & evidence

ORD record
ord-68f4ef4c91db4f9e9604d5416c97b4c0
Source dataset
uspto-grants-2013_01
Patent number
US08349844B2

Reaction notes

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