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

HRID 2382005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382005
[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:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]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:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[CH:19]=[CH:18]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 52239501H-Pyrrolo[2,3-b]pyridin-1-amineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Produkt 1

HCID 250993562-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (1.13 mmol) in EtOAc (20 mL) is added to a stirred solution of pyrrolo[2,3-b]pyridin-1-ylamine (1.13 mmol) and K2CO3 (1.13 mmol) in EtOAc (10 mL) and H2O (20 mL) at rt and the reaction mixture is stirred at rt overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid pyrrolo[2,3-b]pyridin-1-ylamide (305 mg, 81%) as a solid. MS: 334 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.57 (d, H) 7.13-7.55 (m, 4H), 7.99 (m, H), 8.10-8.40 (m, 3H), 9.27 (s, 2H), 12.57 (br, N—H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-82eb4de432ce415ca1be233b23f094b5
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258130B2

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