Chloroacetaldehyde → 8-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 1293692Notes

Reaction equation

HRID 1293692 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[C:4]([NH2:19])=[N:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:8]=1.C([O-])(O)=O.[Na+].Cl[CH2:28][CH:29]=O.O>CCO>[F:21][C:2]([F:1])([F:20])[C:3]1[C:4]2[N:5]([CH:28]=[CH:29][N:19]=2)[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 962WaterHCID 516892Sodium BicarbonateHCID 866116233-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine

Product 1

HCID 866080098-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridineYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 3-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine (12.77 g, 42 mmol) and NaHCO3 (5.96 g, 71 mmol) in EtOH (300 mL) was added chloracetaldehyde solution 55% in water (22 mL, 188 mmol), then refluxed overnight. The reaction mixture was concentrated and purified by column chromatography (CH2Cl2/Et2O 1:1) to give the product as a white crystalline solid (9.6 g, 69%). MS (ISP) 331.1 [(M+H)+].

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography (CH2Cl2/Et2O 1:1)

Sources & evidence

ORD record
ord-9b631330d44344e29053db14df156411
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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