Sodium hydride → 5-methanesulphonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

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Reaction Steps

N-Boc-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (800 mg, 2.94 mmol) was dissolved in DMF (20 mL) and stirred at room temperature. The vessel was flushed with argon and sodium hydride (235 mg, 5.87 mmol) was added. After 30 minutes, the reaction was cooled to 0° C. and methanesulphonyl chloride (0.46 mL, 5.87 mmol) was added dropwise over 5 minutes. The mixture was stirred and allowed to warm to room temperature overnight and the solvent removed in vacuo. TLC and LCMS showed that the BOC group was removed during this process. Therefore the residue was partitioned between 2M aqueous sodium hydroxide (30 mL) and dichloromethane (2×100 mL) and combined organics treated with brine (30 mL), dried (sodium sulphate), concentrated in vacuo. Flash column chromatography (silica, eluting with 100% dichloromethane/5% methanolic ammonia in 50% ethanol/dichloromethane) gave 5-methanesulphonyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as a pale yellow brittle solid (135 mg, 18%).

Provenance & Evidence