Ethyl 5-methyl-1H-pyrazole-3-carboxylate → 5-methyl-1-phenylcarbamoyl-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 499252Notes

Reaction equation

HRID 499252 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.[O-][CH2:13]C.[Na+].BrC[C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C(O)C>[CH2:10]([O:9][C:7]([C:4]1[C:3]([CH3:13])=[C:2]([CH3:1])[N:6]([C:18](=[O:19])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]=1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 77645Ethyl 5-methyl-1H-pyrazole-3-carboxylateHCID 948182-Bromo-N-phenylacetamideHCID 2723922Sodium ethoxide

Product 1

HCID 684171855-methyl-1-phenylcarbamoyl-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a magnetically stirred mixture of ethyl 5-methyl-1H-pyrazole-3-carboxylate (0.02 mol) and sodium ethoxide (0.22 mol) in ethanol (20 mL) is added the title A compound, 2-bromo-N-phenyl-acetamide (0.02 mol). The resulting suspension is stirred at RT for 3 h. After concentration in vacuo, EtOAc is added and the resulting solution is washed twice with water and dried over anhydrous Na2SO4. After filtration and concentration, the residue is purified by flash chromatography (ethyl acetate/hexane) to afford 5-methyl-1-phenylcarbamoyl-methyl-1H-pyrazole-3-carboxylic acid ethyl ester: m.p. 139-140° C.; 1H-NMR (DMSO-d6) δ 1.26-1.29 (t, 3H J=72 Hz), 2.28 (s, 3H), 4.23-4.25 (q, 2H J=72 Hz), δ 06 (s, 2H), δ 6.56 (s, 1H), 7.07 (m, 1H), 7.32 (m, 2H), 7.57 (m, 2H), 10.41 (s, 1H).

Workup

  1. concentrationAfter concentration in vacuo, EtOAc
  2. additionis added
  3. washthe resulting solution is washed twice with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue is purified by flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-15482e95ab144697a2762918a2a667b9
Source dataset
uspto-grants-2010_08
Patent number
US07767685B2

Reaction notes

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