Methyl 2-(triphenyl-lambda~5~-phosphanylidene)propanoate → 2-(5-chloro-3-fluoro-pyridin-2-yl)-4-methyl-5-trifluoromethyl-2H-pyridazin-3-one

HRID 840531Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([F:17])[C:5]([NH:8][N:9]=[CH:10][C:11](=O)[C:12]([F:15])([F:14])[F:13])=[N:6][CH:7]=1.[C:18]([C:22](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:23])(OC)=[O:19]>O1CCOCC1.CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]([F:17])[C:5]([N:8]2[C:18](=[O:19])[C:22]([CH3:23])=[C:11]([C:12]([F:15])([F:14])[F:13])[CH:10]=[N:9]2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 8.09 g 3((5-chloro-3-fluoro-pyridine-2-yl) -hydrazono)-1,1,1-trifluoro-propan-2-one and 11.5 g 1-carbomethoxyethylidene triphenylphosphine in 200 ml dioxane was stired for 30 min. at 20° C. and then heated until complete conversion at 50° C. The reaction mixture was diluted with hexane, filtered from solid triphenylphosphine oxide through silicagel and evaporated. Further purification of the residue on silicagel (ethyl acetate-hexane 3:7) led to the desired product with m.p. 91-93° C.

Workup

filtrationfiltered from solid triphenylphosphine oxide through silicagel
customevaporated
customFurther purification of the residue on silicagel (ethyl acetate-hexane 3:7)

Sources & evidence

ORD record: ord-b041e60a3b4b45a995bedfe6b4d41026
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06369002B1

Reaction notes

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