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Allyl Mercaptan → 4-Allylsulfanylmethyl-6-(2-nitrophenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25818
Notes
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Reaction equation

HRID 25818 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=[C:5]2[CH3:14].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O)([O-:17])=[O:16].CC1(C)C=C(C)C2C(=CC=C(OS(C(F)(F)F)(=O)=O)C=2)N1.C1C(=O)N(Br)C(=O)C1.[CH2:56]([SH:59])[CH:57]=[CH2:58]>>[CH2:56]([S:59][CH2:14][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N+:15]([O-:17])=[O:16])[CH:3]=2)[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=1)[CH:57]=[CH2:58]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 13367Allyl MercaptanHCID 67184N-bromobutanimideHCID 2773548(2-Nitrophenyl)boronic acidHCID 107294646-Bromo-2,2,4-trimethyl-1,2-dihydroquinolineHCID 20760320Trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester

Product 1

HCID 10021826
4-Allylsulfanylmethyl-6-(2-nitrophenyl)-2,2-dimethyl-1,2-dihydroquinoline

Procedure

6-Bromo-2,2,4-trimethyl-1,2-dihydroquinoline was coupled with 2-nitrophenylboronic acid using the procedure described in Example 7 for trifluoromethanesulfonic acid 2,2,4-trimethyl-1,2-dihydroquinolin-6-yl ester. The resulting intermediate was brominated with NBS, followed by the coupling reaction with allyl mercaptan as described in Example 7, to provide 15 mg of the title compound as an oil.

Sources & evidence

ORD record
ord-620b59c3289f49d2a64264d11b6dd951
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06858627B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes