Sodium Carbonate → HCID 10137694, Verbindung

HRID 489576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489576
[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+]>CN(C)C=O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[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 3

HCID 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 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

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). Aqueous sodium carbonate (2 M, 1.15 mL, 2.30 mmol) was added and the reaction was heated to 60° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with 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% of 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 a 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-bb786be3b3024b738c958a37b28d4c54
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977254B2

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