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Water → ethyl 1-({2-[3-chloro-5-(trifluoromethyl)phenyl]-5-methyl-1,3-thiazol-4-yl}methyl)-1H-pyrazole-4-carboxylate

HRID 1257389
ノート
印刷プレビュー

反応式

HRID 1257389 の反応式
Br[C:2]1[S:3][C:4]([CH3:18])=[C:5]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[N:9]2)[N:6]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C(O)C>[Cl:19][C:20]1[CH:21]=[C:22]([C:2]2[S:3][C:4]([CH3:18])=[C:5]([CH2:7][N:8]3[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[N:9]3)[N:6]=2)[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 177502373-Chloro-5-(trifluoromethyl)benzeneboronic acidHCID 58127672ethyl 1-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methyl]-1H-pyrazole-4-carboxylate

生成物 1

HCID 66939532ethyl 1-({2-[3-chloro-5-(trifluoromethyl)phenyl]-5-methyl-1,3-thiazol-4-yl}methyl)-1H-pyrazole-4-carboxylate収率 76%

試薬・触媒・溶媒

1
HCID 20074477Dimethoxyethane ethanol溶媒

反応条件

温度
90 °C

実験手順

Under a nitrogen atmosphere, to a solution of the compound (230 mg, 0.71 mmol) obtained in Example 80e and 3-chloro-5-trifluoromethylphenylboronic acid (210 mg, 0.92 mmol) in 1,2-dimethoxyethane/ethanol (v/v=3/1, 4 mL) were added 2N aqueous sodium carbonate solution (0.71 mL, 1.4 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (60 mg, 0.071 mmol), and the mixture was stirred at 90° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=75/25) to give the title compound (230 mg, 76%) as colorless crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=75/25)

出典と根拠

ORDレコード
ord-8753b1f69abe45e89045e52e43dff940
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461348B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート