C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[C:13]([C:20]([CH3:24])([CH3:23])[C:21]#[N:22])=[N:14][CH:15]=[C:16]([CH2:18][OH:19])[CH:17]=1.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[C:13]([C:20]([CH3:24])([CH3:23])[C:21]#[N:22])=[N:14][CH:15]=[C:16]([CH:18]=[O:19])[CH:17]=1
A solution of oxalyl chloride (0.45 mL, 5.21 mmol) and in dry CH2Cl2 (11 mL), was cooled to −50° C. Dimethyl sulfoxide (0.76 g, 10.87 mmol) was added drop wise at a rapid rate. After 5 minutes, 2-(3-chloro-5-hydroxymethyl-pyridin-2-yl)-2-methyl-propionitrile (0.95 g, 4.53 mmol) from step 1 above, in dry CH2Cl2 (5 mL) was added via cannula followed by triethylamine (3.16 g, 22.65 mmol). The reaction was stirred at −50° C. for 30 additional minutes and then allowed to reach room temperature. The reaction was poured into water (150 mL) and extracted with EtOAc (2×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (0-20% EtOAc in hexanes) to give the product (0.58 g, 62% yield) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 1.90 (s, 6 H), 8.20 (s, 1 H), 8.93 (s, 1H), 10.12 (s, 1 H). ESIMS (MH+): 209.
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