Reaktion #593385

Reaktionsgleichung

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl)nicotinonitrile

1-methylpiperazine

acetic acid

Sodium triacetoxyborohydride

→

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile

Ausbeute 53.2%

Lösungsmittel

THF

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe solution was stirred at room temperature overnight
2. 2
   Einengenconcentrated
3. 3
   workup.ADDITIONAqueous 1N HCl was added
4. 4
   Extraktionthe aqueous phase was extracted with ethyl acetate
5. 5
   workup.ADDITIONby adding sodium carbonate
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe combined organic phases were washed with water and brine
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Einengenconcentrated

Vorschrift

To a stirred solution of 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl)nicotinonitrile (106 mg, 0.25 mmol) in THF (3 mL) and EtOH (1 mL) was added 1-methylpiperazine (75 mg, 0.75 mmol) and acetic acid (75 mg, 1.2 mmol) and the reaction mixture was stirred at room temperature for 1 h. Sodium triacetoxyborohydride (159 mg, 0.75 mmol) was added to the reaction mixture and the solution was stirred at room temperature overnight, and concentrated. Aqueous 1N HCl was added and the aqueous phase was extracted with ethyl acetate, basified to pH of 10 by adding sodium carbonate, and extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over magnesium sulfate, and concentrated to give 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile as a yellow solid (68 mg, 53%). HPLC retention time: 7.0 min.(g); and MS: 511.5 (M+H).

Quelle