反应详情

5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.350 g, 0.900 mmol, 1 eq, Example 56, Step D) was suspended in dioxane (20 mL) under Ar. (R)-2-Pyrrolidine methanol (0.272 g, 2.700 mmol, 3 eq) was added. The reaction mixture was stirred and heated to reflux for 18 hours. Then the reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate (3×). The combined organic phases were washed with brine and dried over Na2SO4. After removing the solvent, the residue was loaded on silica gel and chromatographed, eluting with ethyl acetate/methanol/triethyl amine (100/10/1). 0.200 g (57%) of the indole-amine was obtained as a white solid. This was converted to the .HCl salt. LC/MS (ESI+) 393 (M+1); Anal. Calcd for C24H28N2O3.1HCl.1.25H2O: C, 63.85; H, 7.03; N, 6.20; Found: C, 63.68; H, 6.81; N, 6.20.

1. temperatureheated
2. temperatureto reflux for 18 hours
3. customThen the reaction was quenched with saturated sodium bicarbonate
4. extractionextracted with ethyl acetate (3×)
5. washThe combined organic phases were washed with brine
6. dry with materialdried over Na2SO4
7. customAfter removing the solvent
8. customchromatographed
9. washeluting with ethyl acetate/methanol/triethyl amine (100/10/1)