تفاعل #1159639

معادلة التفاعل

Toluene-4-sulfonic acid (8R)-2-methyl-7,8-dihydro-1,6,9-trioxa-3-aza-cyclo-penta[a]naphthlen-8-ylmethyl ester

3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine

→

title compound

المردود 34.6%

N-[(trans)-3-(5-Fluoro-1H-indol-3-yl)cyclopentyl]-N-{[(8S)-2-methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-yl]methyl}amine

المردود 34.6%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to room temperature
2. 2
   أخرىthe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
3. 3
   غسيلThe organic phase was washed with brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   تركيزconcentrated in vacuo

الإجراء التجريبي

Toluene-4-sulfonic acid (8R)-2-methyl-7,8-dihydro-1,6,9-trioxa-3-aza-cyclo-penta[a]naphthlen-8-ylmethyl ester (0.46 g, 1.2 mmole) and 3-(5-fluoro-1H-indol-3-yl)-cyclopentylamine (0.27 g, 1.2 mmole) were combined in 8 mL of DMSO under nitrogen. This solution was heated to 75-80° C. under nitrogen for 5 hours. After cooling to room temperature, the reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo. Flash chromatography on silica gel (CH2Cl2 then 1% MeOH/CH2Cl2) afforded 0.175 g of the title compound as an off-white solid: m.p. 79-82° C.; MS (ESI) m/z 422 (M+H)+.

المصدر