4-Bromobenzoic acid → 4-bromo-N-cyclopropylbenzamide

HRID 1865858

Reaction equation

HRID 1865858 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2[CH:22]=[CH:23][CH:24]=[N:25]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:25][CH:24]2[CH2:22][CH2:23]2)=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 114644-Bromobenzoic acidHCID 69828CyclopropylamineHCID 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 8829494-bromo-N-cyclopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-benzoic acid (2.5116 g, 12.5 mmol) and HATU (5.2213 g, 13.7 mmol) were dissolved in DMF (40 mL). DIEA (4.572 mL, 26.2 mmol) was added, and the mixture was allowed to stir at ambient temperature for 15 minutes. Then cyclopropylamine (0.866 mL, 12.5 mmol) was added, and the reaction was stirred at ambient temperature overnight. The solvent was removed, and the crude was purified via silica gel chromatography to give the desired product.

Workup

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. customThe solvent was removed
  3. customthe crude was purified via silica gel chromatography

Sources & evidence

ORD record
ord-369d6c7334354de583302be9023cabc1
Source dataset
uspto-grants-2009_12
Patent number
US07629340B2

Linked notes

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