2-Phenylethanethiol → 2,2-Dimethyl-4-phenethylsulfanylmethyl-6-(2-trifluoromethylphenyl)-1,2-dihydroquinoline

HRID 25814Notes

Reaction equation

HRID 25814 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]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][CH:27]=[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>>[CH3:21][C:2]1([CH3:1])[CH:11]=[C:10]([CH2:12][S:43][CH2:42][CH2:41][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23]([F:34])([F:33])[F:22])[CH:8]=2)[NH:3]1

Participants

4

Reactant 3

HCID 781262-PhenylethanethiolHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 20760320Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester

Product 1

HCID 102533962,2-Dimethyl-4-phenethylsulfanylmethyl-6-(2-trifluoromethylphenyl)-1,2-dihydroquinoline

Procedure

Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester was coupled with 2-trifluoromethylphenylboronic acid. Bromination and coupling reaction with 2-phenylethanethiol gave 49 mg of the title compound.

Sources & evidence

ORD record
ord-02ef3f6c42b84d9caaf66c54b9f98454
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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