Sodium Carbonate → 7-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 2223088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223088
Cl[C:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[N:6]([CH3:14])[C:5](=[O:15])[CH2:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>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]>[F:13][C:10]1[CH:11]=[CH:12][C:7]2[N:6]([CH3:14])[C:5](=[O:15])[CH2:4][N:3]=[C:2]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:8]=2[CH:9]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 597138735-Chloro-7-fluoro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Produkt 1

HCID 443661797-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-oneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Versuchsvorschrift

As illustrated in the scheme above and following General Procedure 4, 5-chloro-7-fluoro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (0.201 g, 0.887 mmol), Na2CO3 (0.0940 g, 0.887 mmol), PdCl2(dppf) (0.0362. g, 0.0443 mmol) and phenylboronic acid (0.108 g, 0.886 mmol) were combined and heated for 13 h. After workup, purification of the crude product by silica gel column chromatography (3:1 CH2Cl2:EtOAc) provided the title compound (0.180 g, 76%). 1H-NMR (CDCl3): δ 7.64-7.60 (m, 2H), 7.51-7.45 (m, 1H), 7.44-7.39 (m, 2H), 7.34 (dd, J=4.8 Hz, J=9.2 Hz, 1H), 7.31-7.25 (m, 1H), 7.02 (dd, J=2.8 Hz, J=8.8 Hz, 1H), 4.84 (d, J=10.8 Hz, 1H), 3.78 (d, J=10.8 Hz, 1H), 3.40 (s, 3H). MS (ESI) (M+H)+=269.

Aufarbeitung

  1. temperatureheated for 13 h
  2. customAfter workup, purification of the crude product by silica gel column chromatography (3:1 CH2Cl2:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-94315c751e8b4bf9b15ab6a8f5b6c851
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375101B2

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