4-Toluenesulfonyl chloride → 4-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridine

HRID 930834

Reaktionsgleichung

Reaktionsgleichung von HRID 930834
[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[H-].[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]2[N:10]([S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[CH:11]=[CH:12][C:3]=12

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 118064014-bromo-7-methoxy-1H-pyrrolo[2,3-c]pyridine

Produkt 1

HCID 896575464-bromo-7-methoxy-1-tosyl-1H-pyrrolo[2,3-c]pyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of Example 1b (7.42 g, 32.7 mmol) in dimethylformamide (235 mL) was stirred at room temperature. To this solution was added sodium hydride (1.18 g, 1.96 g of 60% dispersion in oil, 49.0 mmol), and the reaction mixture was stirred for 10 min. P-toluenesulfonyl chloride (9.35 g, 49.0 mmol) was then added portion-wise, and the mixture was stirred at room temperature under nitrogen for 16 hours. The reaction mixture was quenched carefully with water and the resulting beige solid collected by vacuum filtration on a Buchner funnel, and washed with water. The solid was collected and dried in a vacuum oven at 50° C. to provide 12.4 g (100%) of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature under nitrogen for 16 hours
  2. customThe reaction mixture was quenched carefully with water
  3. filtrationthe resulting beige solid collected by vacuum filtration on a Buchner funnel
  4. washwashed with water
  5. customThe solid was collected
  6. customdried in a vacuum oven at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-5728ee9f8abc41cbbb4db3798db6aed7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296741B2

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