N-[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-ethyl]methanesulfonamide → n-[2-(4-Amino-2-butyl-7-vinyl-1h-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide

HRID 9501

Reaction equation

HRID 9501 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH2:23][CH2:24][CH3:25])[N:14]([CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[CH:27]([B-](F)(F)F)=[CH2:28].[K+]>>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][CH2:23][CH2:24][CH3:25])[N:14]([CH2:15][CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH:27]=[CH2:28])=[CH:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 21984323N-[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)-ethyl]methanesulfonamideHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 21984133n-[2-(4-Amino-2-butyl-7-vinyl-1h-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide

Procedure

N-[2-(4-Amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide was coupled with potassium vinyltrifluoroborate according to the procedure described in Part D of Examples 440–455 and recrystallized from acetonitrile to provide N-[2-(4-amino-2-butyl-7-vinyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide as an off-white solid.

Workup

  1. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-3930a4c368c440b2ab323231484fcfea
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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