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

HRID 25812Notes

Reaction equation

HRID 25812 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.[F:22][C:23]1[CH:24]=[CH:25][C:26]([O:32][CH3:33])=[C:27](B(O)O)[CH:28]=1.[C:34]1([CH2:40][CH2:41][SH:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[F:22][C:23]1[CH:24]=[CH:25][C:26]([O:32][CH3:33])=[C:27]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[NH:3][C:2]([CH3:1])([CH3:21])[CH:11]=[C:10]3[CH2:12][S:42][CH2:41][CH2:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:28]=1

Participants

4

Reactant 3

HCID 781262-PhenylethanethiolHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 20760320Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester

Product 1

HCID 103655926-(5-Fluoro-2-methoxyphenyl)-2,2-dimethyl-4-phenethylsulfanylmethyl-1,2-dihydroquinoline

Procedure

Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester was coupled with 5-fluoro-2-methoxyphenylboronic acid. Bromination and coupling reaction with 2-phenylethanethiol gave 20 mg of the title compound.

Sources & evidence

ORD record
ord-6d6d381cb4704b00be7e1b2d6c15c4fa
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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