Water → 1h-Indazole-1-carboxylic acid,3-(3-fluorophenyl)-5-nitro-,1,1-dimethylethyl ester

HRID 503126노트

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HRID 503126 반응식
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:3]=1.[F-:21].[K+].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[F:21][C:5]1[CH:6]=[C:7]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=3)[N:4]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[N:3]=2)[CH:8]=[CH:9][CH:10]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 522689Potassium FluorideHCID 222608361-Boc-3-bromo-5-nitro-1H-indazole

생성물 1

HCID 222608791h-Indazole-1-carboxylic acid,3-(3-fluorophenyl)-5-nitro-,1,1-dimethylethyl ester수율 93.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of 4.5 g of tert-butyl 3-bromo-5-nitro-1H-1-indazolecarboxylate in 20 ml N,N-dimethylformamide were added 2.8 g of 3-fluorophenylboronic aid, 0.16 g of 2-(di-tert-butylphosphino)biphenyl, 60 mg of palladium acetate and 2.31 g of potassium fluoride, and the mixture was heated at 50° C. for two days. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:15), and then recrystallized from diisopropyl ether-hexane, to give 2.2 g of the title compound as a colorless powder.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:15)
  7. customrecrystallized from diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-66e2b16b759c492180a344850c123758
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776890B2

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