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

HRID 25818

Reaktionsgleichung

Reaktionsgleichung von HRID 25818
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]

Komponenten

6

Edukt 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

Produkt 1

HCID 100218264-Allylsulfanylmethyl-6-(2-nitrophenyl)-2,2-dimethyl-1,2-dihydroquinoline

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-620b59c3289f49d2a64264d11b6dd951
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

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