Potassium Carbonate → phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate

HRID 631700ノート

反応式

HRID 631700 の反応式
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([C:13]3([C:16]([F:19])([F:18])[F:17])[CH2:15][CH2:14]3)=[N:8]2)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>C(Cl)Cl>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([N:7]2[C:11]([NH:12][C:28](=[O:29])[O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:10][C:9]([C:13]3([C:16]([F:18])([F:19])[F:17])[CH2:15][CH2:14]3)=[N:8]2)=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 668765651-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

生成物 1

HCID 66876638phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate収率 129.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine (574 mg, 2.0 mmol) in DCM (20 mL) was added K2CO3 (423 mg, 3.06 mmol) and phenyl chloroformate (386 μL, 3.06 mmol). The solution was stirred at rt overnight. The reaction mixture was filtered and the solids washed with DCM, the filtrate concentrated and purified using silica gel chromatography eluting with an EtOAC/Hexane gradient (5-20%) to give phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate (1.04 g, quantitative yield). 1H NMR (300 MHz, DMSO d6) δ 1.33 (m, 4H), 2.34 (s, 3H), 6.51 (s, 1H), 7.12 (m, 2H), 7.23 (m, 1H), 7.37 (m, 6H), 10.13 (s, 1H); LC-MS (ESI) m/z 402 (M+H)+

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with DCM
  3. concentrationthe filtrate concentrated
  4. custompurified
  5. washeluting with an EtOAC/Hexane gradient (5-20%)

出典と根拠

ORDレコード
ord-881dddbd9074421a94d8b9f839a61b72
出典データセット
uspto-grants-2016_04
特許番号
US09320739B2

反応ノート

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