반응 #7052

반응 방정식

sodium sulfate decahydrate

2-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine

HCl

→

2-[3-(2-Fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine hydrochloride

수율 11.0%

용매

ethanol

반응 조건

후처리

1. 1
   기타A dry 25 mL roundbottom flask was equipped with a magnetic stirrer
2. 2
   기타purged with argon gas
3. 3
   workup.ADDITIONTo this was added via syringe a solution of [3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-acetonitrile in 10 mL of anhydrous THF
4. 4
   workup.ADDITIONlithium aluminum hydride solution was added (1 mL of 1M solution in THF) dropwise over 2 minutes via syringe
5. 5
   온도to warm to room temperature
6. 6
   여과filtered through a bed of celite and
7. 7
   농축concentrated in vacuo
8. 8
   기타The resulting residue was purified by flash chromatography (neat CH2Cl2 to 10:1:0.1, CH2Cl2:MeOH:NH4OH over 35 minutes)
9. 9
   기타to give 0.138 g
10. 10
    농축The resulting solution was concentrated in vacuo
11. 11
    기타triturated with 45 mL cold ethyl ether

실험 절차

A dry 25 mL roundbottom flask was equipped with a magnetic stirrer and purged with argon gas. To this was added via syringe a solution of [3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-acetonitrile in 10 mL of anhydrous THF. The flask was cooled to 0° C. and lithium aluminum hydride solution was added (1 mL of 1M solution in THF) dropwise over 2 minutes via syringe. The reaction was allowed to warm to room temperature. After 1 hour, the reaction mixture was combined with 25 mL diethyl ether and quenched with sodium sulfate decahydrate (0.371 g., 1.14 mmol). The resulting suspension was stirred for 2 hours, filtered through a bed of celite and concentrated in vacuo. The resulting residue was purified by flash chromatography (neat CH2Cl2 to 10:1:0.1, CH2Cl2:MeOH:NH4OH over 35 minutes) to give 0.138 g. of the free base 2-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine. The solid was dissolved in 1 mL ethanol, to which was added 0.5 mL of 2N ethanolic HCl. The resulting solution was concentrated in vacuo and triturated with 45 mL cold ethyl ether to give 110 mg of 2-[3-(2-Fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine hydrochloride as a purple powder (11%). (M−H)−=333.

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