4-Chlorophenyl Isocyanate → 3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid (4-chloro-phenyl)-amide

HRID 1820884

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C1C=CC=CC=1.O1CCCC1.CN(C)C1C=CN=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([N:13]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:19]3[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:12]2)=[O:29])=[CH:23][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 200 °C

Versuchsvorschrift

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo-[2,3-b]pyridine 1 (40 mg, 0.16 mmol) was dissolved in benzene and 4-chlorophenyl isocyanate (36 mg, 0.24 mol) dissolved in tetrahydrofuran (4 mL) was added. 4-Dimethylaminopyridine (20 mg, polymer bound) was added. The reaction was heated in a CEM Discover microwave at 200° C. for 10 minutes. The mixture was filtered and concentrated. The resulting solid was washed with a minimum of methanol, filtered, and then washed with dichloromethane to provide 26, (26 mg, 40%). MS(ESI) [M+H+]+=408.4.

Aufarbeitung

additionwas added
filtrationThe mixture was filtered
concentrationconcentrated
washThe resulting solid was washed with a minimum of methanol
filtrationfiltered
washwashed with dichloromethane

Quellen und Nachweise

ORD-Eintrag: ord-e5917b7dd6cc4d92b0244fbf9485412b
Quelldatensatz: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07605168B2

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