تفاعل #46610

معادلة التفاعل

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

المردود 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

المردود 25.0%

المذيبات

propionitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was heated
2. 2
   درجة الحرارةat reflux under argon for 10 h
3. 3
   ترشيحfiltered through supercel
4. 4
   تركيزThe filtrate was concentrated
5. 5
   أخرىthe residue was purified by flash chromatography on silica gel

الإجراء التجريبي

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.

المصدر