Реакция #46610

Уравнение реакции

N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide

6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one

DIEA

tri-o-tolylphosphine

→

title compound

Выход 25.0%

(E)-N-Methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)-acrylamide

Выход 25.0%

Растворители

propionitrile

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураat reflux under argon for 10 h
3. 3
   Фильтрацияfiltered through supercel
4. 4
   КонцентрированиеThe filtrate was concentrated
5. 5
   Другоеthe residue was purified by flash chromatography on silica gel

Методика

A mixture of N-methyl-N-(1,2,7-trimethyl-1H-indol-3-ylmethyl)acrylamide (256 mg, 1 mmole) and 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (227 mg, 1 mmole) in propionitrile (20 mL) was treated with DIEA (0.3 mL), Pd(OAc)2 (29 mg, 0.13 mmole), and tri-o-tolylphosphine (50 mg, 0.16 mmole). The reaction was heated at reflux under argon for 10 h, then was cooled to RT and filtered through supercel. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel to afford the title compound (100 mg, 25%) as an off-white solid: MS (ES) m/e 403.2 (M+H)+. Anal. Calcd for C24H26N4O2.2.75H2O: C, 63.77; H, 7.02; N, 12.39. Found: C, 63.81; H, 7.25; N, 11.90.

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