Sodium hydride → HCID 57537668, Verbindung
Reaktionsgleichung
[Br:1][C:2]1[C:3](Cl)=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:17][OH:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[C:10]3[C:4]=2[C:3]=1[O:18][CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
[2-(5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-phenyl]-methanol (66 mg, 0.2 mmol) was dissolved in 5 mL DMF and NaH was added until the gas evolution stops. The mixture was stirred at 80° C. for 14 h. The reaction was concentrated and quenched with saturated ammonium chloride solution (2 mL) and water (2 mL). The mixture was applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes followed by mass triggered reverse phase HPLC to afford the title compound (1.3 mg, 0.004 mmol, 2.2% yield over 2 steps). 1H NMR (500 MHz, MeCN-d3) δ 8.23 (s, 1H), 7.75 (m, 2H), 7.43 (m, 2H), 7.25 (t, J=7 Hz, 1H), 5.30 (s, 2H). MS: m/z 301.0/303.0 (M+H+).