Sesamol → 3-(5-chloro-4-fluoro-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 1259576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1259576
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:17])[C:5](=[O:16])[N:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(N1C2C(=CC=CC=2)C(=O)C1=O)CCCC.O1C2C=CC(O)=CC=2OC1.[Cl:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][C:46]=1[F:52]>>[Cl:44][C:45]1[C:46]([F:52])=[CH:47][C:48]([OH:51])=[C:49]([C:4]2([OH:17])[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][CH:2]=3)[N:6]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:5]2=[O:16])[CH:50]=1

Komponenten

5

Edukt 4

HCID 68289SesamolHCID 15810921-Pentyl-1H-indole-2,3-dioneHCID 27245234-Chloro-3-fluorophenolHCID 284924584-bromo-1-pentyl-1H-indole-2,3-dione

Produkt 1

HCID 120043063-(5-chloro-4-fluoro-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one

Versuchsvorschrift

Following the procedure as described in PREPARATION 10, and making non-critical variations to replace 4-bromo-1-pentyl-1H-indole-2,3-dione with 1-pentyl-1H-indole-2,3-dione, and 1,3-benzodioxol-5-ol with 4-chloro-3-fluorophenol, the title compound was obtained (33%): 1H NMR (300 MHz, CDCl3) δ 9.80 (s, 1H), 7.52-7.41 (m, 2H), 7.23 (t, 1H), 6.96 (d, 1H), 6.84 (d, 1H), 6.80 (d, 1H), 4.15 (s, 1H), 3.79-3.58 (m, 2H), 1.76-1.62 (m, 2H), 1.40-1.28 (m, 4H), 0.87 (t, 3H); MS (ES+) m/z 346 (M−17), 386 (M+23).

Aufarbeitung

  1. customas described in PREPARATION 10

Quellen und Nachweise

ORD-Eintrag
ord-09f366fd22374b6ca0cf1d5a32f62ed1
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466188B2

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