Sodium methanesulfinate → HCID 66727370, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methyl-propane-2-sulfinic acid [(R)-1-(2-bromopyridin-4-yl)-propyl]-amide (6.00 g, 18.8 mmol) in DMSO (240 mL) is added sodium methanesulfinate (6.77 g, 56.4 mmol) and copper (I) iodide (10.7 g, 56.4 mmol). The mixture is then heated at 130° C. for 45 minutes. The reaction is diluted with saturated aqueous NH4Cl (90 mL), saturated NaHCO3 (10 mL), and EtOAc (150 mL), and sonicated for 10 minutes to dissolve all the solids. The phases are separated and the organic layer is washed with a 9:1 mixture of saturated NH4Cl-saturated NaHCO3 (100 mL). The combined aqueous phases are extracted with EtOAc (150 mL). Combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [(S)-1-(2-methanesulfonyl-pyridin-4-yl)-propyl]-amide as an oil.

Provenance & Evidence