3-Bromo-2-chloropyridine → 3'-[(3-Bromopyridin-2-yl)amino]-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 77726

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)=[O:16])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:28][C:29]1[C:30](Cl)=[N:31][CH:32]=[CH:33][CH:34]=1>CO>[Br:28][C:29]1[C:30]([NH:1][C:2]2[CH:3]=[C:4]([C:8]3[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=4)=[O:16])[CH:9]=3)[CH:5]=[CH:6][CH:7]=2)=[N:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 3′-amino-6-methyl-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide (150 mg, 0.41 mmol) and 3-bromo-2-chloropyridine (90 mg, 0.47 mmol) was heated neat to 180° C. in an oil bath. The temperature was increased to 200° C., and then heating was discontinued and the reaction mixture was allowed to stir for 72 h. The resulting solid was dissolved in methanol and purified by flash column chromatography (eluting with a gradient of 0-40% ethyl acetate in hexanes) to afford product (87 mg, 39%).

Workup

temperatureThe temperature was increased to 200° C.
temperatureheating
custompurified by flash column chromatography (
washeluting with a gradient of 0-40% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-b898b2ff2a2a4343b26a02e88c8107ab
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841318B2

Linked notes

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