Allyl Mercaptan → 4-Allylsulfanylmethyl-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25811Notes

Reaction equation

HRID 25811 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.[CH2:34]([SH:37])[CH:35]=[CH2:36]>>[CH2:34]([S:37][CH2:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]3[CH:24]=[C:23]([F:22])[CH:28]=[CH:27][C:26]=3[O:32][CH3:33])[CH:8]=2)[NH:3][C:2]([CH3:1])([CH3:21])[CH:11]=1)[CH:35]=[CH2:36]

Participants

4

Reactant 3

HCID 13367Allyl MercaptanHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 20760320Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester

Product 1

HCID 104742644-Allylsulfanylmethyl-6-(5-fluoro-2-methoxyphenyl)-2,2-dimethyl-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 allyl mercaptan gave 17 mg of the title compound.

Sources & evidence

ORD record
ord-3be84da476fd47cf9556926b85e65745
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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