3-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamide → 1-(3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanone

HRID 407784Notes

Reaction equation

HRID 407784 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([C:13](N(OC)C)=[O:14])[NH:10][N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH3:19][Mg+].[Br-]>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([C:13](=[O:14])[CH3:19])[NH:10][N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 866840463-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methoxy-N-methyl-1H-pyrazole-5-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 866840471-(3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanoneYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 250-mL round-bottomed flask equipped with a magnetic stirrer was charged with 150c (7.44 g, 1.0 eq., 30.0 mmol) and THF (100 mL). Under N2 protection, a solution of MeMgBr (3.0 Min ether) (25 mL, 2.5 eq., 75.0 mmol) was added at 0° C. The mixture was stirred at room temperature for 5 h and quenched with saturated NH4Cl solution (30 mL). The mixture was concentrated under reduced pressure and the residue was extracted with ethyl acetate (3×50 mL). The combined organic layer was evaporated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 4:1 petroleum ether/ethyl acetate to afford 150d as a white solid (5.40 g, 89%). MS-ESI: [M+H]+ 204.0. 1H NMR (500 MHz, CDCl3) δ 6.74 (s, 1H), 5.92 (s, 2H), 2.61 (s, 3H), 2.15 (s, 6H).

Workup

  1. customA 250-mL round-bottomed flask equipped with a magnetic stirrer
  2. customquenched with saturated NH4Cl solution (30 mL)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate (3×50 mL)
  5. customThe combined organic layer was evaporated under reduced pressure
  6. customthe residue was purified by silica-gel column chromatography
  7. washeluting with 4:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-5e308b61018f4c419a0dae06ed67b7e4
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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