Diisopropylethylamine → 2-bromo-N-(2',4'-dichloro-[1,1'-biphenyl]-4-yl)-4,5-difluorobenzamide

HRID 405202Notes

Reaction equation

HRID 405202 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:27]=1[C:28]([OH:30])=O.CCN(C(C)C)C(C)C.[Cl:46][C:47]1[CH:52]=[C:51]([Cl:53])[CH:50]=[CH:49][C:48]=1[C:54]1[CH:59]=[CH:58][C:57]([NH2:60])=[CH:56][CH:55]=1>CN(C=O)C>[Br:25][C:26]1[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:27]=1[C:28]([NH:60][C:57]1[CH:56]=[CH:55][C:54]([C:48]2[CH:49]=[CH:50][C:51]([Cl:53])=[CH:52][C:47]=2[Cl:46])=[CH:59][CH:58]=1)=[O:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27827892-Bromo-4,5-difluorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 99647252',4'-Dichloro-[1,1'-biphenyl]-4-amine

Product 1

HCID 710598662-bromo-N-(2',4'-dichloro-[1,1'-biphenyl]-4-yl)-4,5-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Solid HATU (501 mg, 1.3 mmol) was added to a DMF solution (1 mL) of 2-bromo-4,5-difluorobenzoic acid (250 mg, 1.1 mmol), i-Pr2NEt (0.5 mL, 3.2 mmol), and 2′,4′-dichloro-[1,1′-biphenyl]-4-amine (251 mg, 1.1 mmol) and the resulting mixture was stirred at room temperature. After 2 h the resulting mixture was directly purified via column chromatography to yield the title compound.

Workup

  1. customAfter 2 h the resulting mixture was directly purified via column chromatography

Sources & evidence

ORD record
ord-6b98ecef57a34f1a915b0653d220e2ad
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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