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

HRID 1428111ノート

反応式

HRID 1428111 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)]

出典と根拠

ORDレコード
ord-e137cd6a2e4146a59f6aa467d85ab756
出典データセット
uspto-grants-2015_01
特許番号
US08933103B2

反応ノート

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