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0 °C

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.

1. customA dry 25 mL roundbottom flask was equipped with a magnetic stirrer
2. custompurged with argon gas
3. 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. additionlithium aluminum hydride solution was added (1 mL of 1M solution in THF) dropwise over 2 minutes via syringe
5. temperatureto warm to room temperature
6. filtrationfiltered through a bed of celite and
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified by flash chromatography (neat CH2Cl2 to 10:1:0.1, CH2Cl2:MeOH:NH4OH over 35 minutes)
9. customto give 0.138 g
10. concentrationThe resulting solution was concentrated in vacuo
11. customtriturated with 45 mL cold ethyl ether