Ethyl Acetate → HCID 10137694, Verbindung

HRID 1793968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1793968
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][C:18]=3[O:33][CH3:34])=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CN(C)C=O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:23][C:21]1[C:20]([C:41]2[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]=2)=[CH:19][C:18]([O:33][CH3:34])=[C:17]([CH:22]=1)[C:15]([N:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH2:10][N:4]2[CH:3]=[CH:2][CH:1]=[C:5]2[CH2:6]1)=[O:16]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 3194401-Cyclohexenyl trifluoromethanesulfonateHCID 22219703[10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl][5-chloro-2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]methanone

Produkt 1

HCID 10137694HCID 10137694, VerbindungAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 53485975CID 53485975KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[5-chloro-2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Step E (0.220 g, 0.459 mmol), cyclohex-1-en-1-yl trifluoromethanesulfonate (0.116 g, 0.505 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.011 g, 0.014 mmol) were combined in N,N-dimethylformamide (2.3 mL). 2 M aqueous sodium carbonate (1.15 mL, 2.30 mmol) was added and the reaction heated to 60° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. Flash column chromatography on silica gel eluting with a solvent gradient from 30 to 40% ethyl acetate in hexane afforded the title compound (0.140 g) as an oil. The oil was dissolved in diethyl ether/petroleum ether and concentrated to afford an amorphous white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a1c26244ee59418fa1242b21780e5514
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07022699B2

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