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Ethanol → 1'-(4-Fluorophenyl)-2-methyl-1'H,2H-3,4'-bipyrazole

HRID 238372
ノート
印刷プレビュー

反応式

HRID 238372 の反応式
I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O.C1(C)C=CC=CC=1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([C:2]3[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=3)[CH:17]=[N:16]2)=[CH:11][CH:10]=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

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 133340655-Iodo-1-methyl-1H-pyrazoleHCID 467386841-(4-Fluorophenyl)pyrazole-4-boronic acid

生成物 1

HCID 866848711'-(4-Fluorophenyl)-2-methyl-1'H,2H-3,4'-bipyrazole収率 64.4%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (600 mg), [1-(4-fluorophenyl)-1H-pyrazol-4-yl]boronic acid (650 mg), tetrakistriphenylphosphine palladium (166 mg), 2 M sodium carbonate aqueous solution (2.9 mL), ethanol (3.0 mL) and toluene (6.0 mL) was stirred at 100° C. for 4 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was concentrated under a reduced pressure, and the residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to ethyl acetate), so as to obtain the title compound (450 mg) in the form of a light yellow solid.

後処理

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under a reduced pressure
  3. customthe residue was then purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1 to ethyl acetate)

出典と根拠

ORDレコード
ord-ffefd9914333427893e53e9a6ac5a748
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642626B2

反応ノート

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