Methyl chloroformate → 3,3a,4,5-tetrahydro-3a-methoxycarbonyl-N-[4'-(trifluoromethyl)phenyl]-2H-benz[g]indazole-2-carboxamide

HRID 2396077

Reaktionsgleichung

C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]([F:38])([F:37])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([N:24]2[CH2:32][CH:31]3[C:26]([C:27]4[CH:36]=[CH:35][CH:34]=[CH:33][C:28]=4[CH2:29][CH2:30]3)=[N:25]2)=[O:23])=[CH:17][CH:16]=1.Cl[C:40]([O:42][CH3:43])=[O:41]>C1COCC1.CCCCCC>[CH3:43][O:42][C:40]([C:31]12[CH2:30][CH2:29][C:28]3[CH:33]=[CH:34][CH:35]=[CH:36][C:27]=3[C:26]1=[N:25][N:24]([C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([F:13])([F:37])[F:38])=[CH:20][CH:19]=1)=[O:23])[CH2:32]2)=[O:41]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 0.9 ml of diisopropylamine in 10 ml of THF, at -78°C., was added 2.3 ml of 2.5 M n-butyl lithium in hexane and the mixture wasstirred for 5 mins. To this solution was added a solution of 1.0 g of the title compound of Step A in 5 ml of THF. The reaction was warmed to 0° C., recooled to -78° C. and then 0.75 ml of methyl chloroformate was added. The reaction mixture was then stirred for 24 h, with gradual warming to room temperature, quenched with 0.5 ml of glacial acetic acid, and poured into a 5% solution of aqueous NaHCO3. The mixture was extracted with chloroform, dried over magnesium sulfate and concentrated. Chromatography on silica gel with 30% ethyl acetate hexane afforded 0.25 g of the title compound, m.p. 177° to 180° C.

Aufarbeitung

customrecooled to -78° C.
temperaturewith gradual warming to room temperature
customquenched with 0.5 ml of glacial acetic acid
additionpoured into a 5% solution of aqueous NaHCO3
extractionThe mixture was extracted with chloroform
dry with materialdried over magnesium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-88dc0f73e0bb490381b6c96a8d352748
Quelldatensatz: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05491162

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