Reaktion #1588008

Reaktionsgleichung

24

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

trans-2-pentenoic acid

EDC.HCl

HOBt

DIPEA

→

Compound 26

Ausbeute 11.7%

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

Ausbeute 11.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefor completion of the reaction
2. 2
   Sonstigequench the reaction mixture with dilute water
3. 3
   workup.ADDITIONThe organic layer was treated with ethyl acetate (25 mL)
4. 4
   Waschenwas washed with brine solution (25 mL)
5. 5
   Trocknendried over sodium sulphate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto get the crude product
9. 9
   SonstigeThe resulting oil was purified through silica gel chromatography

Vorschrift

A solution of 24 (50 mg, 0.2242 mmol) and trans-2-pentenoic acid 25 (24.6 mg, 0.246 eq) in DMF was added EDC.HCl (33 mg, 0.2706 mmol) and HOBt (36.5 mg, 0.2706 mmol). DIPEA (57.9 mg, 0.448 eq) was added to the reaction, stirred 12 h at RT and check the TLC for completion of the reaction and quench the reaction mixture with dilute water. The organic layer was treated with ethyl acetate (25 mL) and was washed with brine solution (25 mL) and dried over sodium sulphate, filtered and concentrated to get the crude product. The resulting oil was purified through silica gel chromatography using a gradient of 4% Ethyl acetate:hexane to afford 8 mg of Compound 26. MS-ES+305.1 1H NMR (400 MHz, DMSO-D6-d6): 11.45 (s, 1H), 10.08 (s, 1H), 8.40 (s, 1H), 8.17 (s, 1H), 7.85 (d, 1H), 7.61 (m, 1H), 7.36 (m, 2H), 7.30 (d, 1H), 5.62 (m, 1H), 2.35 (s, 3H).

Quelle