Benzophenone imine → 1-Cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

HRID 1507605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507605
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH3:16])([CH3:15])[C:9](=[O:14])[N:10]([CH:11]3[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[C:17]1([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[NH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[CH:11]1([N:10]2[C:4]3[CH:3]=[C:2]([N:24]=[C:23]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:7]=[CH:6][C:5]=3[C:8]([CH3:16])([CH3:15])[C:9]2=[O:14])[CH2:13][CH2:12]1

Komponenten

8

Edukt 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 900475066-chloro-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

Produkt 1

HCID 900475681-Cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)KatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 6-chloro-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (1.789 g, 7.56 mmol), diphenylmethanimine (2.05 g, 1.9 ml, 11.3 mmol, Eq: 1.5) and sodium tert-butoxide (1.23 g, 12.8 mmol) in toluene (48 ml) were added tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (156 mg, 151 mol) and BINAP (94.1 mg, 151 mol). The reaction mixture was heated to 100° C. for 18 hours and then diluted with dichloromethane. Silica gel was added and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel using heptane/EtOAc as eluent. The title compound was obtained as brown crystals (2.31 g).

Aufarbeitung

  1. additionSilica gel was added
  2. customthe solvent was evaporated
  3. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0a8c236c365f44ffa09cc015dfbee393
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221816B2

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