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

HRID 2299840Notes

Reaction equation

HRID 2299840 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-α]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-α]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-f2c2a46666b14819a905bec173cfcc41
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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