3-Fluorobenzaldehyde → Methyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-fluorophenyl)pyridine-5-carboxylate

HRID 247115

Reaktionsgleichung

Reaktionsgleichung von HRID 247115
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1)[C:2]([CH3:4])=O.[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25]>C(O)(C)C>[CH3:4][C:2]1[NH:21][C:22]([CH3:28])=[C:23]([C:24]([O:26][CH3:27])=[O:25])[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=2)[C:1]=1[C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1

Komponenten

5

Edukt 3

HCID 680093-FluorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Produkt 1

HCID 135833461Methyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-fluorophenyl)pyridine-5-carboxylateAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A stirred solution of 500 mg of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 390 mg of 3-fluorobenzaldehyde and 362 mg of methyl 3-aminocrotonate in 20 ml of isopropyl alcohol was heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel using chloroform as eluent to give 780 mg of methyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-fluorophenyl)pyridine-5-carboxylate. Recrystallization from ethyl acetate-isopropyl ether afforded pale yellow crystals, m,p, 186° C.

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8919eabfded0477495c00523c7ca0a08
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705786

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