3-Bromopyridine → 4-(6-Nitro-1-pyridin-3-yl-1H-indol-3-yl)-benzonitrile

HRID 2079895

Reaktionsgleichung

[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1.CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CN(C=O)C>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:14]=[CH:15][C:16]([C:17]#[N:18])=[CH:19][CH:20]=3)=[CH:9][N:10]2[C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

Method K Combine 4-(6-nitro-1H-indol-3-yl)-benzonitrile, 9 (265 mg, 1.0 mmol), potassium phosphate tribasic (513 mg, 2.4 mmol), copper (I) iodide (38 mg, 0.2 mmol), and 2 mL of DMF in a 4 mL vial. Add 3-bromopyridine (120 μL, 1.2 mmol) and rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (127 μL, 0.8 mmol). Warm the solution to 110° C. Let the solution stir overnight. Let the solution cool to RT, isolate the yellow precipitate by filtration, and wash the precipitate sequentially with DMF, 1:1 DMF:H2O, H2O, DMF, EtOAc, and then hexanes. Dry the precipitate under vacuum to yield 301 mg, 0.88 mmol, 88% of the title compound. LRMS (API ES+)=341.0 (M+H).

Aufarbeitung

temperaturecool to RT
customisolate the yellow precipitate
filtrationby filtration
washwash the precipitate sequentially with DMF, 1:1 DMF
customDry the precipitate under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-cf259c33132b43c5a3e2d84a878695a7
Quelldatensatz: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07932284B2

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