(5-chloro-1H-indol-2-yl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl 5-chloro-2-indole-carboxylate (1 eq) was dissolved in THF (0.45M) under N2. This solution was cooled to 0° C. for fifteen minutes and then 1.1 eq LiAlH4 (1M in THF) was added. The resulting dark brown solution was allowed to return to rt with stirring and kept overnight. Then water (1/25 of the volume of the LiAlH4 solution) was added slowly, followed by 15% NaOH(aq) (1/25 of the volume of the LiAlH4 solution) solution. Finally, water (1/25 of the volume of the LiAlH4 solution) was added along with a large amount of MgSO4. Solution was filtered and the solid was washed with EtOAc and the filtrate was collected. Solvent was stripped off to give (5-chloro-1H-indol-2-yl)methanol (yellow solid) in 85% yield. to return to rt Solution was filtered the solid was washed with EtOAc the filtrate was collected

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (5-chloro-1H-indol-2-yl)-methanol (3.6 g, 0.02 mol), Ce2CO3 (13 g, 0.04 mol) in 100 mL of DMF which was cooled to 0° C., was added methanesulfonyl-ethene (2.1 g, 0.02 mol) in portions. The reaction mixture was stirred at a temperature between 30° C. and 50° C. overnight. Ice-water was then added to the mixture, the precipitate was filtered and dried to give [5-chloro-1-(2-methanesulfonyl-ethyl)-1H-indol-2-yl]-methanol (2 g, yield: 34.7%). the precipitate was filtered dried