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

HRID 550577

Reaction equation

[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

Participants

Conditions

Temperature: 150 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-c245e1be8ece41e185316c67078959bf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947685B2

Linked notes

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