6-Bromo-4-chloroquinoline → (6-Bromoquinolin-4-yl)-[3-(tert-butyl-dimethylsilanyloxy)phenyl]amine

HRID 1675718Notes

Reaction equation

HRID 1675718 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2Cl.[Si:13]([O:20][C:21]1[CH:22]=[C:23]([NH2:27])[CH:24]=[CH:25][CH:26]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[NH:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([O:20][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[CH:22]=1

Participants

3

Reactant 2

HCID 51395376-Bromo-4-chloroquinolineHCID 143147823-((Tert-butyldimethylsilyl)oxy)aniline

Product 1

HCID 57857960(6-Bromoquinolin-4-yl)-[3-(tert-butyl-dimethylsilanyloxy)phenyl]amineYield 80.2%

Procedure

6.26 g (25.8 mmol) of 6-bromo-4-chloroquinoline are reacted by method A with 7.5 g (33.6 mmol) of 3-(tert-butyldimethylsilanyloxy)phenylamine. 8.9 g (20.7 mmol, 80%) of the desired product are obtained.

Sources & evidence

ORD record
ord-884f174bc6174d6c9dbd5a739790d11d
Source dataset
uspto-grants-2011_08
Patent number
US08003787B2

Reaction notes

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