Sodium Methoxide → 3-(2-Chlorophenyl)-6-(2,4-difluorophenoxy)-4-methyl-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

HRID 2114560Notes

Reaction equation

HRID 2114560 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[C:13](=[O:26])[N:12]([CH3:27])[C:11]=2[C:10]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])=[N:9]1)=O)(C)(C)C.C[O-].[Na+]>CO>[Cl:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:10]1[C:11]2[N:12]([CH3:27])[C:13](=[O:26])[C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[CH:15][C:16]=2[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 598127853-(2-Chlorophenyl)-6-(2,4-difluorophenoxy)-4-methyl-5-oxo-4,5-dihydro-pyrazolo[4,3-b]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 598129693-(2-Chlorophenyl)-6-(2,4-difluorophenoxy)-4-methyl-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-oneYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the crude 3-(2-chlorophenyl)-6-(2,4-difluorophenoxy)-4-methyl-5-oxo-4,5-dihydro-pyrazolo[4,3-b]pyridine-1-carboxylic acid tert-butyl ester (0.0298 mmol) in a solution of 0.5 M sodium methoxide in methanol (Aldrich) (7 mL) was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure at 55° C., and the resulting residue was diluted with ethyl acetate (35 mL) and water (25 mL). The organic layer was separated, washed with brine (1×25 mL), dried over magnesium sulfate, filtered, concentrated, and purified by Preparative Thin Layer Chromatography eluting with 60% ethyl acetate in hexanes to give the title compound (5.2 mg, (M+H)+=388) as a white powder.

Workup

  1. customThe solvent was removed under reduced pressure at 55° C.
  2. additionthe resulting residue was diluted with ethyl acetate (35 mL) and water (25 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (1×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by Preparative Thin Layer Chromatography
  9. washeluting with 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d36c12790919425b8be9c29a1e4f6a65
Source dataset
uspto-grants-2008_10
Patent number
US07435731B2

Reaction notes

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