5-Bromo-1-methyl-1H-imidazole → 7-chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

HRID 418577

Reaktionsgleichung

Reaktionsgleichung von HRID 418577
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](CCCC)(CCCC)CCCC)[S:10][C:3]=12.Br[C:25]1[N:29]([CH3:30])[CH:28]=[N:27][CH:26]=1>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>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:25]3[N:29]([CH3:30])[CH:28]=[N:27][CH:26]=3)[S:10][C:3]=12

Komponenten

5

Edukt 2

HCID 15152585-Bromo-1-methyl-1H-imidazoleHCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

Produkt 1

HCID 222500727-chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridineAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Nitrogen was bubbled through a mixture of the tin derivative 6 (7.19 g, 15.7 mmol) and 5-bromo-1-methyl-1H-imidazole (2.02 g, 12.5 mmol) [a) Begtrup, M.; Larsen, P.; Acta Chem. Scand. 44, 10; 1990; 1050-1057. b) Begtrup, M.; Bull. Soc. Chim. Belz.; 97; 8-9; 1988; 573-598. c) Begtrup, M.; Larsen, P.; Chem. Pharm. Bull. 42, 9; 1994; 1784-1790.] in toluene (20 mL) for 5 minutes. Pd(PPh3)4 (1.50 g, 1.30 mmol) was added and nitrogen was bubbled for additional 5 minutes. Finally, the mixture was refluxed under nitrogen overnight, the resultant yellow suspension was concentrated under reduced pressure and then purified with flash chromatography (eluent EtOAc/MeOH 90:10), to afford title compound 16 as a yellow solid (2.48 g, 79% yield). MS (m/z): 250.0 (M+H).

Aufarbeitung

  1. customnitrogen was bubbled for additional 5 minutes
  2. temperatureFinally, the mixture was refluxed under nitrogen overnight
  3. concentrationthe resultant yellow suspension was concentrated under reduced pressure
  4. custompurified with flash chromatography (eluent EtOAc/MeOH 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-76872375db744658ac8ab55943ac7a15
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093264B2

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