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A mixture of 3-(6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)propane-1,2-diol (100 mg, 0.31 mmol) and TEA (94 mg, 0.93 mmol) in THF (6 mL) was stirred under N2 at 0° C., MsCl (36 mg, 0.31 mmol) was added dropwise. The reaction was stirred at 0° C. for 1 h and RT overnight. Water was added and after extraction with EA, the organic layer was washed with water, brine, dried over Na2SO4 and concentrated on a rotary evaporator. The residue was purified by column chromatography (PE:EA=2:1˜1:1) to give the product of 3-(6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl)-2-hydroxypropyl methanesulfonate (60 mg, yield: 48%). 1H-NMR (MeOD, 400 MHz) δ 7.80 (d, J=7.6 Hz, 1H), 7.26˜7.32 (m, 2H), 7.09˜7.11 (m, 1H), 7.04 (s, 1H), 6.70 (t, J=7.6 Hz, 1H), 4.20˜4.29 (m, 3H), 3.09˜3.13 (m, 5H). MS (M+H)+: 399/401.

1. stirringThe reaction was stirred at 0° C. for 1 h and RT overnight
2. extractionafter extraction with EA
3. washthe organic layer was washed with water, brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated on a rotary evaporator
6. customThe residue was purified by column chromatography (PE:EA=2:1˜1:1)