Triethylamine → Carbonic acid 3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-ylmethyl ester 4-nitro-phenyl ester

HRID 585158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585158
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C@@:8]2([F:24])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][OH:22])[C:9]2=[O:23])[CH:7]=1.C(N(CC)CC)C.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=1)=[O:36]>ClCCl>[N+:44]([C:41]1[CH:40]=[CH:39][C:38]([O:37][C:35](=[O:36])[O:22][CH2:21][N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=3)[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:25][CH3:26])([F:24])[C:9]2=[O:23])=[CH:43][CH:42]=1)([O-:46])=[O:45]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 69331104HCID 69331104, Verbindung

Produkt 1

HCID 20822786Carbonic acid 3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-ylmethyl ester 4-nitro-phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 25 mL round bottom flask containing (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-1-hydroxymethyl-6-trifluoromethyl-1,3-dihydro-indol-2-one ((S)-IV) (0.397 g, 1.02 mmol) was added 5 mL anhydrous dichloromethane, triethylamine (0.204 g, 2.04 mmol), and 4-nitrophenyl chloroformate (0.246 g, 1.22 mmol). The reaction was allowed to stir overnight at room temperature, affording carbonic acid 3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-ylmethyl ester 4-nitro-phenyl ester (VIII), after which 2-aminoethanol (0.186 g, 3.05 mmol) was added and the reaction was allowed to stir for an additional 24 hours. The solvent was removed in vacuo, and the crude residue was purified by column chromatography (silica gel; 1:1 Hex:EtOAc to 4:1 EtOAc:Hex) producing 0.250 g (51%) of the title compound. 1H NMR (CDCl3 400 MHz): δ=7.78 (s,1H), 7.51 (s, 1H), 7.33 (d, 2H, J=7 Hz), 7.22 (d, 1H, J=7 Hz), 6.74 (d, 1H, J=7 Hz), 5.88 (d, 1H, J=12 Hz), 5.83 (d, 1H, J=12 Hz), 3.75 (m, 2H), 3.50 (s, 3H), 3.39 (m, 2H, J=7 Hz).

Quellen und Nachweise

ORD-Eintrag
ord-21b5e8098a0e4276b4e2eca8f8c9678f
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06930100B2

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