Sodium Carbonate → 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-chlorobiphenyl-2-yl) amide

HRID 346814ノート

反応式

HRID 346814 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][N:14]([CH3:16])[CH:15]=1)=[O:10].[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9]([C:11]2[C:12]([C:17]([F:20])([F:19])[F:18])=[N:13][N:14]([CH3:16])[CH:15]=2)=[O:10])=[CH:24][CH:23]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 179479961-Methyl-3-trifluoromethyl-1h-pyrazole-4-carboxylic acid(2-bromo-phenyl)amide

生成物 1

HCID 587994761-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (4'-chlorobiphenyl-2-yl) amide

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid(2-bromo-phenyl)amide (0.64 g), 4-chlorobenzene boronic acid (0.29 g), powdered sodium carbonate (0.25 g) and tetrakis(triphenylphosphine) palladium (0.04 g) in 25 ml 1,2-dimethoxyethane (DME) and 2 ml water is heated at reflux temperature for 20 hours. After cooling, the solvent is removed in a water jet vacuum and the residue taken up in ethylacetate/water. The ethylacetate phase is washed twice with water and brine and then dried over sodium sulfate. Distilling off the solvent left the raw material which can be further purified by column chromatography (silicagel; eluant: ethylacetate/hexane 1:1) or recrystallization from TBME/hexane. The yield after purification is 0.6 g; m.p.=145–146° C.

後処理

  1. temperatureat reflux temperature for 20 hours
  2. temperatureAfter cooling
  3. customthe solvent is removed in a water jet vacuum
  4. washThe ethylacetate phase is washed twice with water and brine
  5. dry with materialdried over sodium sulfate
  6. distillationDistilling off the solvent
  7. waitleft the raw material which
  8. customcan be further purified by column chromatography (silicagel; eluant: ethylacetate/hexane 1:1) or recrystallization from TBME/hexane
  9. customThe yield
  10. customafter purification

出典と根拠

ORDレコード
ord-6c221704ba22411d94f61e1a06afe252
出典データセット
uspto-grants-2007_02
特許番号
US07173055B1

反応ノート

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