Potassium Carbonate → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide

HRID 2382007

Reaktionsgleichung

Reaktionsgleichung von HRID 2382007
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N:17]1([NH2:26])[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[N:17]1([NH:26][C:14]([C:11]2[CH:10]=[N:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:13][CH:12]=2)=[O:15])[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 19601545Pyrrolo[3,2-b]pyridin-1-ylamineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Produkt 1

HCID 250993572-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamideAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (0.45 mmol) in EtOAc (8 mL) is added to a stirred solution of pyrrolo[3,2-b]pyridin-1-ylamine (0.45 mmol) and K2CO3 (0.45 mmol) in EtOAc (4 mL) and H2O (8 mL) at rt, and the reaction mixture is stirred at rt for 30 min. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[3,2-b]pyridin-1-ylamide (116 mg, 77%) as a solid. MS: 334 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.60 (d, H) 7.15-7.60 (m, 4H), 8.01 (m, H), 8.10-8.41 (m, 3H), 9.27 (s, 2H), 12.45 (br, N—H). IC50=18 nM.

Aufarbeitung

  1. customEtOAc is evaporated in vacuo
  2. filtrationthe resulting solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-43b0fa9bfc384c69b0ed237aa200b5dc
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

Verknüpfte Notizen

Wird geladen…