تفاعل #46596

معادلة التفاعل

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

N-(1H-indol-3-ylmethyl)-N-methylacrylamide

tri-ortho-tolylphosphine

diisopropylethylamine

→

title compound

المردود 37.0%

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

المردود 37.0%

المذيبات

propionitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةto reflux under N2 overnight
3. 3
   ترشيحThe dark mixture was filtered through a pad of Celite®
4. 4
   غسيلthe filter pad was rinsed with acetonitrile (250 mL)
5. 5
   تركيزThe filtrate was concentrated in vacuo
6. 6
   أخرىthe residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3)

الإجراء التجريبي

A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.64 g, 2.80 mmole), N-(1H-indol-3-ylmethyl)-N-methylacrylamide (0.60 g, 2.80 mmole), Pd(OAc)2 (0.06 g, 0.28 mmole), tri-ortho-tolylphosphine (0.17 g, 0.56 mmole) and diisopropylethylamine (0.73 mL, 4.2 mmole) in propionitrile (50 mL) was deoxygenated, then was heated to reflux under N2 overnight. The dark mixture was filtered through a pad of Celite®, and the filter pad was rinsed with acetonitrile (250 mL). The filtrate was concentrated in vacuo, and the residue was purified by flash chromatography on silica gel (10% MeOH/CHCl3). The title compound (0.37 g, 37%) was obtained as a light yellow solid after drying in vacuo: MS (ES) m/e 361 (M+H)+.

المصدر