Potassium Carbonate → 3-Ethynyl-5-(4-fluoro-phenyl)-1-methyl-1H-pyrazole

HRID 1984690Notes

Reaction equation

HRID 1984690 reaction equation
[CH3:1]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH3:25])[N:23]=[C:22]([CH:26]=O)[CH:21]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:26]([C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[N:24]([CH3:25])[N:23]=1)#[CH:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 288086345-(4-Fluorophenyl)-1-methyl-1H-pyrazole-3-carboxaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 866169083-Ethynyl-5-(4-fluoro-phenyl)-1-methyl-1H-pyrazoleYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.27 g, 11.8 mmol) in methanol (100 mL) were added 5-(4-fluoro-phenyl)-1-methyl-1H-pyrazole-3-carbaldehyde (may be prepared in analogy to WO2005014553, 2.00 g, 9.8 mmol) and potassium carbonate (2.84 g, 20.56 mmol) and the resulting yellow suspension was stirred for 19 h at ambient temperature. After extraction with aqueous sodium hydrogencarbonate and ethyl acetate the combined organic layers were washed with brine, dried over sodium sulfate. Concentration and purification by chromatography (SiO2, hexane:ethyl acetate=100:0 to 75:25) afforded the title compound (1.83 g, 93%) as a white solid. MS: m/e=201.3 [M+H]+.

Workup

  1. extractionAfter extraction with aqueous sodium hydrogencarbonate and ethyl acetate the combined organic layers
  2. washwere washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration and purification by chromatography (SiO2, hexane:ethyl acetate=100:0 to 75:25)

Sources & evidence

ORD record
ord-052be45920924404ac618607eb98fd77
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

Loading…