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

HRID 503126ノート

反応式

HRID 503126 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 27342152-(Di-tert-butylphosphino)biphenyl触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66e2b16b759c492180a344850c123758
出典データセット
uspto-grants-2010_08
特許番号
US07776890B2

反応ノート

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