2-Phenylethanethiol → 6-(2,5-Dimethoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline

HRID 25804

Reaction equation

HRID 25804 reaction equation
[CH3:1][C:2]1([CH3:21])[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](OS(C(F)(F)F)(=O)=O)[CH:8]=2)[NH:3]1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1B(O)O.[C:35]1([CH2:41][CH2:42][SH:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([CH3:1])([CH3:21])[CH:11]=[C:10]2[CH2:12][S:43][CH2:42][CH2:41][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 781262-PhenylethanethiolHCID 27343422,5-Dimethoxyphenylboronic acidHCID 20760320Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester

Product 1

HCID 103434956-(2,5-Dimethoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline

Procedure

Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester was coupled with 2,5-dimethoxyphenylboronic acid. Bromination and coupling reaction with 2-phenylethanethiol gave 43 mg of the title compound.

Sources & evidence

ORD record
ord-c246b091f79b4c109a44240105e7ca29
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Linked notes

Loading…