methyl 3-formyl-1H-indole-6-carboxylate → methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate

HRID 1749746Notizen

Reaktionsgleichung

[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.[CH:26]([C:28]1[C:36]2[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=O>CO.N1CCCCC1>[C:22]([O:21][C:19]([N:16]1[CH2:15][CH2:14][N:13]([CH2:12][C:3]2[C:4]3[O:8]/[C:7](=[CH:26]\[C:28]4[C:36]5[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=5)[NH:30][CH:29]=4)/[C:6](=[O:9])[C:5]=3[CH:10]=[CH:11][C:2]=2[OH:1])[CH2:18][CH2:17]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.060 g, 0.017 mmol) obtained in Example A16, Step 1 in methanol (2.0 mL) was added with methyl 3-formyl-1H-indole-6-carboxylate (0.040 g, 0.019 mmol). Then, the mixture was added with 5 drops of piperidine, and the mixture was stirred at 60° C. for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (93:7)) to obtain methyl (Z)-3-[(7-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-6-hydroxy-3-oxobenzofuran-2(3H)-ylidene)methyl]-1H-indole-6-carboxylate (0.071 g, 78%).

Aufarbeitung

customThe solvent was evaporated under reduced pressure
washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (93:7))

Quellen und Nachweise

ORD-Eintrag: ord-5bcdab5a84964c73825988766249b75f
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09156827B2

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