Dichloromethane → 1-[(4-Methoxy)phenyl]-3-[E-2-(methoxycarbonyl)ethenyl]-1H-pyrazole

HRID 610153Notes

Reaction equation

HRID 610153 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11](NCC(OC)=O)=[N:10]2)=[CH:5][CH:4]=1.C1(P(=[CH:39][C:40]([O:42][CH3:43])=[O:41])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:44](Cl)Cl>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11](/[CH:44]=[CH:39]/[C:40]([O:42][CH3:43])=[O:41])=[N:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 865879801-[(4-Methoxy)phenyl]-3-[(methoxycarbonyl)methylamino]-1H-pyrazole

Product 1

HCID 865879821-[(4-Methoxy)phenyl]-3-[E-2-(methoxycarbonyl)ethenyl]-1H-pyrazoleYield 83%

Procedure

To a solution of 1-[(4-methoxy)phenyl]-3-(carboxaldehyde) -1H-pyrazole-5-[(2'-tert-butylaminosulfonyl-[1,1']-biphen-4-yl)carboxyamide (1.30 g, 2.44 mmol) in 30 mL of methylene chloride was added methyl (triphenylphosphoranylidene)acetate (0.98 g, 2.92 mmol). The mixture was allowed to stir at ambient temperature for 18 h. The volatiles were removed in vacuo and the residue was purified by flash chromatography (elution with 1:1 ethyl acetate/hexane) to afford 1.2 g (83%) of the title compound. LRMS (ES+): 589.1 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by flash chromatography (elution with 1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-afe099391a6a4d33a39d75267b1c7af9
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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