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

HRID 1984690ノート

反応式

HRID 1984690 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-052be45920924404ac618607eb98fd77
出典データセット
uspto-grants-2009_06
特許番号
US07544704B2

反応ノート

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