Aniline → 3-Phenylamino-pyrazine-2-carboxylic acid (2-methyl-pyridin-4-yl)-amide

HRID 550577

反応式

HRID 550577 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16](Br)=[N:15][CH:14]=[CH:13][N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[C:16]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][CH:14]=[CH:13][N:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 6115AnilineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 665243483-bromo-N-(2-methylpyridin-4-yl)pyrazine-2-carboxamide

生成物 1

HCID 119966313-Phenylamino-pyrazine-2-carboxylic acid (2-methyl-pyridin-4-yl)-amide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

3-Bromo-pyrazine-2-carboxylic acid (2-methyl-pyridin-4-yl)-amide (130 mg, 0.44 mmol) and aniline (54 mg, 0.58 mmol) were dissolved in 4 mL dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (51 mg, 0.09 mmol), cesium carbonate (290 mg, 0.89 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (46 mg, 0.044 mmol) were added and the reaction mixture was stirred under microwave irradiation for 50 minutes at 150° C. The reaction mixture was then evaporated and purified by flash chromatography on silica gel (heptane/ethyl acetate 1:1->100% ethyl acetate). The desired product was obtained as a yellow solid (47 mg, 35%), MS: m/e=306.2 (M+H+).

後処理

  1. customThe reaction mixture was then evaporated
  2. custompurified by flash chromatography on silica gel (heptane/ethyl acetate 1:1->100% ethyl acetate)

出典と根拠

ORDレコード
ord-c245e1be8ece41e185316c67078959bf
出典データセット
uspto-grants-2011_05
特許番号
US07947685B2

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