1-(4-Fluorophenyl)ethylamine → Methyl 3-bromo-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoate

HRID 1454209Notes

Reaction equation

HRID 1454209 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:39][C:40]1[CH:45]=[CH:44][C:43]([CH:46]([NH2:48])[CH3:47])=[CH:42][CH:41]=1>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:7])[NH:48][CH:46]([C:43]2[CH:44]=[CH:45][C:40]([F:39])=[CH:41][CH:42]=2)[CH3:47])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 1230631-(4-Fluorophenyl)ethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 57529327Methyl 3-bromo-5-((1-(4-fluorophenyl)ethyl)-carbamoyl)benzoateYield 99.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-5-(methoxycarbonyl)benzoic acid (0.60 g, 2.32 mmol) and HATU (1.06 g, 2.78 mmol) in DMF (15 mL) was stirred at room temperature for 10 min. Then 1-(4-fluorophenyl)ethanamine (0.323 g, 0.3 mL, 2.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O (3 times) and brine, dried over sodium sulfate, and concentrated under vacuum to give the title compound (0.880 g, 99.9% yield): HPLC retention time: 2.098 min (method A). MS (ESD) (M+H)+ 380/382.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washwashed with H2O (3 times) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2d7e6210521646458e46bcb27ad5be6c
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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