Water → 3-(4-Aminophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 1428111노트

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HRID 1428111 반응식
O.C(=O)([O-])[O-].[K+].[K+].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([NH2:22])=[N:17][CH:18]=[C:19](Br)[CH:20]=2)=[CH:11][CH:10]=1.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1>O1CCOCC1.C(Cl)(Cl)Cl.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>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([NH2:22])=[N:17][CH:18]=[C:19]([C:27]3[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=3)[CH:20]=2)=[CH:11][CH:10]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 682889763-(4-Aminophenyl)-5-bromopyridin-2-amine

생성물 1

HCID 867000643-(4-Aminophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine수율 57.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Water (5 ml), potassium carbonate (1742 mg) and tetrakis(triphenylphosphine)palladium (242 mg) were added to a solution of the compound obtained in Step 1 of Example 1 (1110 mg) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (874 mg) in 1,4-dioxane (50 ml), and the mixture was stirred at 100° C. for five hours. After leaving to cool, the reaction solution was diluted with chloroform. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=96:4 (v/v)] to give 638 mg of the title compound as a solid.

후처리

  1. customAfter leaving
  2. temperatureto cool
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [chloroform:methanol=96:4 (v/v)]

출처 및 근거

ORD 기록
ord-e137cd6a2e4146a59f6aa467d85ab756
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933103B2

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