CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1[CH:14]=[C:15]([N:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=1.N#N.C([O-])(O)=O.[Na+]>C(Cl)Cl.C(OCC)C>[CH:12]([C:13]1[CH:14]=[C:15]([N:19]([CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=1)=[O:11]Into a −78° C. solution of DMSO (20.8 mL, 0.269 mole, 3.1 eq) in DCM (460 mL) was added oxalyl chloride (16 mL, 0.109 mole, 1.25 eq) dropwise and stirred for 15 minutes. N-(3-(Hydroxymethyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (26.4 g, 0.86 mole, 1 eq) was added dropwise via addition funnel as a solution in DCM (146 mL). The reaction mixture was stirred for 30 min. then TEA (102 mL, 1 mole, 11.7 eq) was added via addition funnel. The reaction mixture was allowed to warmed to 0° C. with an ice bath and stirred for 1 hour with a N2 sweep through a bleach/caustic scrubber. The reaction mixture was poured into saturated NaHCO3 and diluted with diethyl ether (2000 mL). The layers were separated and the aqueous layer backextracted with diethyl ether (1000 mL). The combined organics were washed with brine (1000 mL), dried with MgSO4, filtered and concentrated. The residue was purified by flash chromatography, eluting with 1:1 DCM/EtOAc to give the title compound as a white solid (15.0 g, 57.2).
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