Ethyl Acetate → LY 393558

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3,4-dihydro-3-(1-methylethyl)-6-methylsulfonyl-1H-2,1,3-benzothiadiazine-2,2-dioxide (0.38 g, 0.00125 mol), triphenylphosphine (0.39 g, 0.0015 mol) and 2-(4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl)ethanol (0.26 g, 0.0015 mol) in DMF (10 ml) at −5° C. was added dropwise under nitrogen diethyl azodicarboxylate (0.24 ml, 0.0015 mol). The reaction was stirred at −5° C. for 10 mins then allowed to warm to room temperature stirring for a further 20 mins. After the addition of ethyl acetate (30 ml) and water (20 ml), the organic layer was washed with water (4×20 ml) the organics dried (MgSO4) and concentrated in vacuo to afford 0.52 g of 1-[2-[4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-3,4-dihydro-3-(1-methylethyl)-6-methylsulfonyl-1H-2,1,3-benzothiadiazine-2,2-dioxide as a yellow solid. Mp 118-120° C.

Provenance & Evidence