Dimethylformamide → 6-Cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 2382962노트

반응식

HRID 2382962 반응식
[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21](Br)[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:33][N:34](C=O)C>[Cl-].[NH4+].C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C-]#N.[Zn]>[CH3:1][NH:2][S:3]([C:6]1[CH:32]=[CH:31][C:9]([CH2:10][NH:11][C:12]([C:14]2[C:15]3[CH:16]=[N:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21]([C:33]#[N:34])[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

참가 물질

9

반응물 2

HCID 6228DimethylformamideHCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

생성물 1

HCID 442515866-Cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

시약·촉매·용매 6

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 152416121,1`-Bis(diphenylphosphino)ferrocene촉매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

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온도
120 °C

실험 절차

A mixture of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide (0.04 g, 0.08 mmol), Pd2(dba)3 (0.009 g, 0.01 mmol), 1,1-bis(diphenylphosphino)ferrocene (dppf) (0.005 g, 0.01 mmol), zinc cyanide (0.01 g, 0.09 mmol) and zinc powder (0.002 g, 0.02 mmol) were charged in a sealed tube with anhydrous DMF (3 mL) at room temperature. The reaction mixture was heated at 120° C. for 3 hours. The solution was cooled to room temperature and diluted with saturated aqueous ammonium chloride (10 mL) and ethyl acetate (20 mL). The organic layer was separated and washed with brine (10 mL) and dried over sodium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 20-70% ethyl acetate in hexanes to afford the title compound.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of 20-70% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-6a9792b36ac14c2096c9dbbfc035e3cd
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263597B2

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