Dimethylformamide → methyl (4E)-4-[[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl]methoxyimino]-4-phenylbutanoate

HRID 584486Notes

Reaction equation

HRID 584486 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1.[OH:12][C:13]1[CH:34]=[CH:33][C:16]([CH2:17][O:18]/[N:19]=[C:20](/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)\[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[N:4]1[C:3]([CH2:2][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:17][O:18]/[N:19]=[C:20](/[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)\[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:33][CH:34]=2)=[CH:11][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridineHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoate

Product 1

HCID 22344637methyl (4E)-4-[[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl]methoxyimino]-4-phenylbutanoateYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 2-chloromethylimidazo[1,2-a]pyridine (293 mg), methyl E-4-(4-hydroxybenzyloxyimino)-4-phenylbutyrate (500 mg), potassium carbonate (442 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 17 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (321 mg, yield 45%) as a colorless oil from an ethyl acetate-hexane (3:2, v/v)-eluted fraction.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8b971db0b5394018a070ed8ed45407f7
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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