Sodium Carbonate → HCID 59127378, 화합물

HRID 2246612노트

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HRID 2246612 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]2.[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28](B(O)O)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]4)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 21914527(5-(Cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)boronic acidHCID 228320255-Bromo-1H-indazole, N1-BOC protected2회

생성물 1

HCID 59127378HCID 59127378, 화합물수율 211.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of tert-butyl 5-bromo-1H-indazole-1-carboxylate (Intermediate 1, 1.07 g), {5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}boronic acid (0.85 g), sodium carbonate (1.9 g) and tetrakis(triphenylphosphine)palladium(0) (0.42 g) in 1,2-dimethoxyethane (70 ml) was stirred at reflux under nitrogen for 20 h. The solvent was removed and the residue was partitioned between water (50 ml) and ethyl acetate (50 ml). The aqueous layer was re-extracted with ethyl acetate (3×30 ml) and the combined organic extracts were dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40) to give the title compound (3.1 g).

후처리

  1. temperatureat reflux under nitrogen for 20 h
  2. customThe solvent was removed
  3. customthe residue was partitioned between water (50 ml) and ethyl acetate (50 ml)
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (3×30 ml)
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40)

출처 및 근거

ORD 기록
ord-a3e918193024463c81fd82d719a78adb
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687532B2

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