Benzyl Bromide → 4-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester

HRID 250457

Reaktionsgleichung

Reaktionsgleichung von HRID 250457
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:19])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10]([Br:19])[C:11]2[C:16]([C:17]=1[O:18][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 860145411-Bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester

Produkt 1

HCID 860145034-Benzyloxy-1-bromo-isoquinoline-3-carboxylic acid butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (6.48 g, 20 mmol; Example D-28 a), benzyl bromide (3.6 ml, 30 mmol), K2CO3 (12.44 g, 90 mmol) and acetone (300 ml) was refluxed with stirring for 2.5 d. The solvent was then evaporated in vacuo. To the residue was added water (100 ml) and the mixture was extracted with EtOAc (100 ml). The organic phase was dried over MgSO4 and evaporated in vacuo to give the title compound as a yellowish solid; MS-(+)-ion: M+1=414.1.

Aufarbeitung

  1. customThe solvent was then evaporated in vacuo
  2. additionTo the residue was added water (100 ml)
  3. extractionthe mixture was extracted with EtOAc (100 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fc8d1a74afb84d69a3ef9241881514b9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863292B2

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