4-Bromoaniline → (2R)-N-(4-bromophenyl)-2-(4-fluorophenyl)propanamide

HRID 1051871Notes

Reaction equation

HRID 1051871 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(=O)(O)[O-].[Na+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:9](=[O:11])[C@@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH3:12])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 78074-BromoanilineHCID 516892Sodium BicarbonateHCID 7005040(R)-2-(4-fluorophenyl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89924420(2R)-N-(4-bromophenyl)-2-(4-fluorophenyl)propanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2R)-2-(4-fluorophenyl)propanoic acid (30.79 g) and 4-bromoaniline (30.0 g) in dimethylformamide (522 g) were added sodium bicarbonate (43.9 g) and HATU (99.5 g). The mixture was stirred at room temperature overnight. Then water (1000 g) was added followed by stirring at room temperature for 1 h. The precipitated solid was collected by filtration and washed with water (500 g) and dried by 50° C. in the vacuum overnight to give 52.59 g (93.6% of theory) of the title compound.

Workup

  1. stirringby stirring at room temperature for 1 h
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water (500 g)
  4. customdried by 50° C. in the vacuum overnight

Sources & evidence

ORD record
ord-c798b2c31b8c46f39de052306bdfe37b
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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