تفاعل #313121

معادلة التفاعل

N-(1,3-dimethyl-1H-indol-2-ylmethyl)-N-methylacrylamide

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

DIEA

tri-o-tolylphosphine

→

title compound

المردود 59.1%

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

المردود 59.1%

المذيبات

propionitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was purged with argon
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةat reflux for 16 hr
4. 4
   تركيزconcentrated under vacuum
5. 5
   أخرىPurification by flash chromatography on silica gel (5% methanol/CHCl3)
6. 6
   ترشيحtrituration with ethyl acetate, filtration
7. 7
   أخرىdrying under vacuum

الإجراء التجريبي

To a stirred solution of N-(1,3-dimethyl-1H-indol-2-ylmethyl)-N-methylacrylamide (1.7 g, 7 mmole) in propionitrile (50 mL) was added 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (1.16 g, 5.1 mmole), DIEA (1.8 mL, 10.3 mmole), palladium(II) acetate (112 mg, 0.5 mmole), and tri-o-tolylphosphine (304 mg, 1.0 mmole). The reaction was purged with argon and heated at reflux for 16 hr, then was cooled to RT and concentrated under vacuum. Purification by flash chromatography on silica gel (5% methanol/CHCl3). trituration with ethyl acetate, filtration, and drying under vacuum gave the title compound (1.17 g, 59%) as an off-white solid: LCMS (ES) m/e 389.2 (M+H)+.

المصدر