2,3-Dibromothiophene → 3-Bromo-2-(2-fluoropyridin-3-yl)thiophene

HRID 580821

Reaktionsgleichung

Reaktionsgleichung von HRID 580821
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[Br:7].[F:8][C:9]1[C:14]([Sn](CCCC)(CCCC)CCCC)=[CH:13][CH:12]=[CH:11][N:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN1CCCC1=O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[C:14]1[C:9]([F:8])=[N:10][CH:11]=[CH:12][CH:13]=1

Komponenten

7

Edukt 3

HCID 765902,3-DibromothiopheneHCID 2724141Tetrabutylammonium FluorideHCID 110903192-Fluoro-3-(tributylstannyl)pyridine

Produkt 1

HCID 154085683-Bromo-2-(2-fluoropyridin-3-yl)thiopheneAusbeute 40,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 2,3-dibromothiophene (2.86 g), 2-fluoro-3-tributylstannylpyridine (3.93 g), Pd(Ph3P)2Cl2 (0.153 g) in N-methylpyrrolidinone (25 mL) was heated at 75° C. under argon for 3.5 hours. Tetrabutylammonium fluoride (1M in tetrahydrofuran, 10 mL) was added and the mixture was stirred for 3 hours. The mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. Chromatography of the residue over silica gel gave 3-bromo-2-(2-fluoropyridin-3-yl)thiophene (1.07 g) as an oil.

Aufarbeitung

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-74d82bbcf3e24e00a96e5df58432d02b
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919779

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