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

HRID 346814

반응식

HRID 346814 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c221704ba22411d94f61e1a06afe252
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173055B1

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