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Water → Ethyl (2E)-3-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-5-yl]-2-propenoate

HRID 1639822
Notes
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Reaction equation

HRID 1639822 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.O.O.O.C([O-])(=O)C.[Na+].[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[CH:24]=[CH2:25].O>CN(C)C(=O)C>[F:12][C:11]([F:14])([F:13])[C:9]1[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2](/[CH:25]=[CH:24]/[C:23]([O:27][CH2:28][CH3:29])=[O:26])[N:7]2[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8821Ethyl AcrylateHCID 23665404Sodium Acetate TrihydrateHCID 59334526HCID 59334526, compound

Product 1

HCID 66720629Ethyl (2E)-3-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-5-yl]-2-propenoateYield 63%

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine (10.0 g, 37.7 mmol) in N,N-dimethylacetamide (60 mL) were added sodium acetate trihydrate (6.19 g, 75.0 mmol), ethyl acrylate (4.94 mL, 45.3 mmol) and [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (2.76 g, 3.77 mmol) at room temperature, and the mixture was stirred under nitrogen stream at 110° C. for 24 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (6.74 g, yield 63%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

Sources & evidence

ORD record
ord-7f5a096da6cb470da4c300a7e194e1ef
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08110585B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes