4-Bromoaniline → N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzamide

HRID 1410227Notes

Reaction equation

HRID 1410227 reaction equation
[F:1][CH:2]([F:19])[CH2:3][O:4][C:5]1[CH:13]=[C:12]([NH:14][CH3:15])[C:11]([N+:16]([O-:18])=[O:17])=[CH:10][C:6]=1[C:7]([OH:9])=O.[Br:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:7](=[O:9])[C:6]2[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[C:12]([NH:14][CH3:15])=[CH:13][C:5]=2[O:4][CH2:3][CH:2]([F:1])[F:19])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595298542-(2,2-Difluoroethoxy)-4-(methylamino)-5-nitrobenzoic acid

Product 1

HCID 59529852N-(4-bromophenyl)-2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The sub-title compound was prepared in accordance with Example 72, step (c) using 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoic acid (800 mg; 2.90 mmol), 4-bromoaniline (499 mg; 2.90 mmol), HBTU (1.10 g; 2.90 mmol), TEA (587 mg; 5.80 mmol) and DMF (15 mL). Yield: 1.01 g (81%).

Sources & evidence

ORD record
ord-3e98a095978440038ad997a9b8de99e7
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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