[Cl:1][C:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][S:4][N:3]=1.[C:13]1([O:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:23][Mg]I.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:6]([C:7]2[CH:12]([CH3:23])[CH:11]=[CH:10][N:9]([C:20]([O:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:21])[CH:8]=2)=[N:5][S:4][N:3]=1
A solution of cuprous iodide (0.40 g, 2 mmol) in dry THF (50 ml) was stirred under nitrogen for 10 min. A solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (J.Med.Chem. 1992, 35, 2274-2283) (9.9 g, 50 mmol) in dry THF (150 ml) was added to the reaction, then cooled to -25° C. Phenylchloroformate (6.3 ml, 50 mmol) in THF (20 ml) was added slowly. The reaction mixture was stirred at -25° C. for 30 min., then allowed to warm to room temperature and stirred for another 2.5 h. The reaction mixture was cooled to -25° C. and methylmagnesium iodide (55 mmol in 20 ml ether) was added. The reaction mixture was stirred for 20 min., 20% NH4Cl(aq) (100 ml) was added and then extracted with ether (200 ml). The combined organic phases were washed with 20% NH4Claq :NH4OH (1:1) (50 ml), water (50 ml), 4N HCl (50 ml), water (50 ml) and brine (50 ml). The organic phases were dried and evaporated to give crude title compound. Purification on column chromatography, eluent: toluene, gave the title compound in 11.9 g (71%) yield.
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