Dimethylamine → 3-Bromo-α-fluoro-N,N-dimethylbenzeneacetamide

HRID 886632Notes

Reaction equation

HRID 886632 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([F:12])[C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13][NH:14][CH3:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([F:12])[C:9]([N:14]([CH3:15])[CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534101951071455-00-9

Product 1

HCID 598248883-Bromo-α-fluoro-N,N-dimethylbenzeneacetamideYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3-bromo-phenyl)-fluoro-acetic acid (436 mg, 1.9 mmol), dimethyl amine (1.9 ml, 3.7 mmol-2M solution in THF), HATU (1.1 g, 2.8 mmol), DIEA (0.7 ml, 3.7 mmol) in DMF were stirred at room temperature overnight. The reaction was diluted with ethyl acetate, washed with 1N HCl, saturated Na2HCO3, brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2-(3-bromo-phenyl)-2-fluoro-N,N-dimethyl-acetamide (212 mg, 44% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.86 (d, 6H), 6.40-6.44 (d, 1H), 7.41 (m, 1H), 7.45 (d, 1H), 7.642 (m, 2H). MS: m/z 261.1 (M+H+).

Workup

  1. washwashed with 1N HCl, saturated Na2HCO3, brine
  2. dry with materialdried with Na2SO4
  3. customdecanted
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bf6a4297c77442e78334f657c70871d4
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

Loading…