반응 #1159639

반응 방정식

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

수율 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

수율 34.6%

용매

DMSO

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후처리

1. 1
   온도After cooling to room temperature
2. 2
   기타the reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
3. 3
   세척The organic phase was washed with brine
4. 4
   건조dried over magnesium sulfate
5. 5
   농축concentrated in vacuo

실험 절차

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)+.

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