N-bromobutanimide → ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate

HRID 2199741Notes

Reaction equation

HRID 2199741 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.[Br:12]N1C(=O)CCC1=O>CC#N>[Br:12][C:3]1[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5][NH:6][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 77645Ethyl 5-methyl-1H-pyrazole-3-carboxylate

Product 1

HCID 616098ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 5-methyl-1H-pyrazole-3-carboxylate (3.24 g) in CH3CN (25 mL) was treated with N-bromosuccinimide (3.92 g) at 0° C. The solution was stirred at room temperature for 2 hours. The solvent was removed, and the residue was purified by flash chromatography on silica gel (ethyl acetate in hexanes) to give the title compound. 1H NMR (500 MHz, DMSO-d6): 13.61 (s, 1H), 4.27 (q, J=6.75 Hz, 2H), 2.21 (s, 3H), 1.28 (t, J=7.06 Hz, 3H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography on silica gel (ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-147628184e1440b0973b11a9d20210ea
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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