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

HRID 394810Notes

Reaction equation

HRID 394810 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-23d5a74a84a04143af9a884be99da5a1
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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