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

HRID 1984690노트

반응식

HRID 1984690 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-052be45920924404ac618607eb98fd77
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544704B2

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