(1,1'-Biphenyl)-4-carboxylic acid → N-(4-bromobenzyl)biphenyl-4-carboxamide

HRID 711221Notes

Reaction equation

HRID 711221 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[Br:49][C:50]1[CH:55]=[CH:54][C:53]([CH2:56][NH2:57])=[CH:52][CH:51]=1>CN(C=O)C.C(OCC)(=O)C>[Br:49][C:50]1[CH:55]=[CH:54][C:53]([CH2:56][NH:57][C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:6][CH:5]=2)=[O:9])=[CH:52][CH:51]=1

Participants

7

Reactant 4

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 775714-BromobenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67208625N-(4-bromobenzyl)biphenyl-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of biphenyl-4-carboxylic acid 10-2 (0.89 g, 4.5 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (1.7 g, 4.5 mmol) and DIEA (2.34 mL, 13.5 mmol) in DMF (15.0 mL) was added (4-bromophenyl)methanamine 10-1 (1.0 g, 4.5 mmol) at room temperature. The reaction was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture, and the resulting precipitate was collected by vacuum filtration to give N-(4-bromobenzyl)biphenyl-4-carboxamide 10-3 as a white solid. MS m/z 366.2 (M+1).

Workup

  1. filtrationthe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-4b6330016db44e57ad6d3c8f956b49e1
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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