Reaktion #1588015

Reaktionsgleichung

(E)-4-(dimethylamino)but-2-enoic acid

(E)-4-(dimethylamino)but-2-enoic acid hydrochloride

diethyl amine

3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline

EDC.HCl

→

(E)-4-(dimethylamino)-N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-enamide

Lösungsmittel

water

THF DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous was extracted with 10% methanol in chloroform for two times
2. 2
   TrocknenThe organic layer was dried over sodium sulphate
3. 3
   Einengenconcentrated
4. 4
   Sonstigeto get the crude
5. 5
   SonstigeThe crude was purified through flash chromatography
6. 6
   WaschenThe compound was eluted in 2% methanol in chloroform as half white solid (E)-4-(dimethylamino)-N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-enamide 152

Vorschrift

A solution of 3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)aniline 24 (100 mg 0.449 mmol) was dissolved in THF/DMF was added diethyl amine (71.46 mg, 0.89 mmol). EDC.HCl (139.19 mg, 0.89 mmol) was added to the reaction then (E)-4-(dimethylamino)but-2-enoic acid 131 (103.8 mg, 0.6292 mmol) was added to the reaction and stirred at RT for overnight. After completion the reaction was diluted with water and the aqueous was extracted with 10% methanol in chloroform for two times. The organic layer was dried over sodium sulphate and concentrated to get the crude. The crude was purified through flash chromatography by using neutral alumina. The compound was eluted in 2% methanol in chloroform as half white solid (E)-4-(dimethylamino)-N-(3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)but-2-enamide 152. MS-ES+334.9, 1H NMR (400 MHz, DMSO): 11.35 (s, 1H), 10.14 (s, 1H), 8.42 (d, 1H), 8.07 (d, 1H), 7.98 (s, 1H), 7.63 (m, 1H), 7.39 (d, 1H), 7.27 (s, 1H), 6.73 (m, 1H), 6.29, (d, 1H), 3.27 (m, 1H), 3.05 (d, 2H), 2.29 (s, 3H), 2.17 (s, 6H).

Quelle