Sodium Carbonate → 1-(4-Fluoro-phenyl)-6-methyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 2382965노트

반응식

HRID 2382965 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]B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[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]([CH3:33])[CH:22]=2)=[O:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

생성물 1

HCID 581387941-(4-Fluoro-phenyl)-6-methyl-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

A mixture of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide (0.05 g, 0.1 mmol), methylboronic acid (0.01 g, 0.2 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol) and a solution of 2 N aqueous sodium carbonate (0.1 mL, 0.2 mmol) was added in a sealed tube with DMF (5 mL). The tube was capped and the resulting solution was degassed with argon for 5 minutes. The reaction was heated to 120° C. by microwave irradiation for 2.5 hours. The reaction was cooled to room temperature and quenched with saturated aqueous ammonium chloride (5 mL) and diluted with ethyl acetate (20 mL). The organic layer was separated, washed with brine (10 mL) and dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 20-50% ethyl acetate in hexanes to afford the title compound.

후처리

  1. customThe tube was capped
  2. customthe resulting solution was degassed with argon for 5 minutes
  3. temperatureThe reaction was cooled to room temperature
  4. customquenched with saturated aqueous ammonium chloride (5 mL)
  5. additiondiluted with ethyl acetate (20 mL)
  6. customThe organic layer was separated
  7. washwashed with brine (10 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with a gradient of 20-50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-43237c5c6a5f4337b479ffb09f5cea87
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263597B2

반응 노트

불러오는 중…