Reaktion #2337611

Reaktionsgleichung

1H-Pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid 5-methyl ester

1-Isopropyl-piperidin-4-ylamine hydrochloride

BOP-Cl

water

→

2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester

Lösungsmittel

DMF

NEt3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionwas extracted with ethyl acetate (3×150 ml)
2. 2
   WaschenThe combined organic layers were washed with brine (1×50 ml)
3. 3
   Trocknendried over MgSO4
4. 4
   FiltrationAfter filtration the solvent
5. 5
   Sonstigewas removed under reduced pressure
6. 6
   Sonstigethe residue was purified by chromatography on silica gel eluting with EtOAc/MeOH 9:7->EtOAc/MeOH/NH3(aq.) 6:4:0.04
7. 7
   workup.ADDITIONThe fractions containing the product
8. 8
   Sonstigewere evaporated

Vorschrift

To a solution of 9.5 g 1H-Pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid 5-methyl ester in 120 mL DMF and 23.9 mL NEt3, 9.2 g 1-Isopropyl-piperidin-4-ylamine hydrochloride and 11 g BOP-Cl were added at RT and the mixture was stirred for 3 h. After addition of 20 mL of water the reaction mixture was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (1×50 ml) and then dried over MgSO4. After filtration the solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel eluting with EtOAc/MeOH 9:7->EtOAc/MeOH/NH3(aq.) 6:4:0.04. The fractions containing the product were evaporated and codestilled with toluene. Yield: 7.2 g.

Quelle