N,O-Dimethylhydroxylamine → 4-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamide

HRID 2401435Notes

Reaction equation

HRID 2401435 reaction equation
[Br:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][N:5]([CH3:7])[CH:6]=1.F[B-](F)(F)F.[N:16]1([O:25][C:26](N(C)C)=[N+](C)C)[C:20]2C=CC=CC=2N=N1.CNOC>C(N(CC)C(C)C)(C)C.CN(C)C=O>[Br:1][C:2]1[C:3]([C:8]([N:16]([O:25][CH3:26])[CH3:20])=[O:10])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

6

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 5360134-bromo-1-methyl-1H-pyrazole-3-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 866667294-bromo-N-methoxy-N,1-dimethyl-1H-pyrazole-3-carboxamideYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A mixture of 4-bromo-1-methyl-1H-pyrazole-3-carboxylic acid (2.04 g, 10 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (3.21 g, 10 mmol), N,O-dimethylhydroxylamine (1.22 g, 20 mmol) in N,N-Diisopropylethylamine (5 mL) and N,N-Dimethylformamide (20 mL) was stirred for 12 h at room temperature. The mixture was concentrated in vacuum, and the residue was purified by flash chromatography eluting with petroleum ether/ethyl acetate=5:1 to give the titled product as a colorless oil (2.4 g, 97%). LC/MS m/z 247 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated in vacuum
  2. customthe residue was purified by flash chromatography
  3. washeluting with petroleum ether/ethyl acetate=5:1

Sources & evidence

ORD record
ord-52498883c49e465bb6ba9f4319315a5d
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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