Methanesulfonic Acid → Methyl 2-(3-chloropropoxy)indole-3-carboxylate

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A suspension of methyl indole-3-carboxylate (5.25 g, 30.0 mmol) and DABCO (1.84 g, 16.4 mmol) in dry CH2Cl2 (25 ml) was cooled to 0° C. under argon atmosphere, treated in one portion with NCS (4.41 g, 33.0 mmol) and the mixture stirred for 10 min. The resulting solution was added to a solution of 3-chloropropan-1-ol (3.12 g, 33.0 mmol) in dry CH2Cl2 (25 ml) containing anhydrous methane sulphonic acid (0.23 ml). The resulting suspension was stirred for 30 min and then washed with 10% aqueous Na2CO3 solution (3×25 ml). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The resulting oil was triturated with toluene (10 ml) at 0° C. for 1 h and the solid precipitate filtered, washed with a small amount of toluene and dried in vacuo to leave the product as an off-white solid (5.22 g, 65.0%).

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