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

HRID 2186247Notes

Reaction equation

HRID 2186247 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.[CH3:20][O:21][C:22](=[O:43])[CH:23]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=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:23]/[C:22]([O:21][CH3:20])=[O:43])=[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-daf44ad7f298470d878937d424dd050d
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Reaction notes

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