Reaktionsgleichung
[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.[CH3:17][S:18]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([NH2:30])[CH:25]=[CH:24]2)(=[O:20])=[O:19].C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.O>[CH3:17][S:18]([C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[N:26]([NH:30][C:14]([C:11]1[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]=1)=[O:15])[CH:25]=[CH:24]2)(=[O:20])=[O:19]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (0.62 mmol) in EtOAc (10 mL) is added to a stirred solution of 5-methanesulfonyl-indole-1-ylamine (0.62 mmol) and K2CO3 (3.08 mmol) in EtOAc (10 mL) and H2O (10 mL) at 0° C., and the reaction mixture is warmed to rt and stirred overnight. EtOAc is evaporated in vacuo, and the resulting solid is collected by filtration. The solid is triturated with DCM to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-1-yl)-amide (85 mg, 34%) as a solid. MS: 411 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.13 (s, 3H), 6.81 (m, H) 7.25-7.39 (m, H), 7.49-7.67 (m, 3H), 7.72-7.84 (m, H), 8.21-8.32 (m, 2H), 8.39 (d, H), 9.41 (s, 2H).
Aufarbeitung
- customEtOAc is evaporated in vacuo
- filtrationthe resulting solid is collected by filtration
- customThe solid is triturated with DCM
Quellen und Nachweise
- ORD-Eintrag
- ord-e2042f2ffaa4442298f6d57d1bcaf63b
- Quelldatensatz
- uspto-grants-2012_09
- Patentnummer
- US08258130B2
Verknüpfte Notizen
Wird geladen…