Tributyl(prop-1-yn-1-yl)stannane → Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylate

HRID 129416

Reaktionsgleichung

Reaktionsgleichung von HRID 129416
Br[C:2]1[C:3]([F:22])=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]2=[O:20].[CH2:23]([Sn](CCCC)(CCCC)C#CC)[CH2:24][CH2:25]C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([N:10]2[C:11]3[C:6](=[CH:5][C:4]([F:21])=[C:3]([F:22])[C:2]=3[C:23]#[C:24][CH3:25])[C:7](=[O:20])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9]2)[CH2:14][CH2:13]1

Komponenten

5

Edukt 2

HCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 11046932Ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Produkt 1

HCID 131719208Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylateAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

7.5 g of ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 9.1 g of 1-tributylstannyl-prop-1-ine and 1.16 g of tetrakis(triphenylphosphine)palladium(0) are refluxed for 8 hours in 80 ml of absolute toluene under a nitrogen atmosphere. The solid which crystallises out at -18° C. is filtered off with suction and dried. 2.05 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-(propin-1-yl)-3-quinolinecarboxylate are obtained (31% of theory).

Aufarbeitung

  1. customThe solid which crystallises out at -18° C.
  2. filtrationis filtered off with suction
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4800a91c1bd1403db3585adca1dff293
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468742

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