[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.[N:19]1([O:28][C:29](N(C)C)=[N+](C)C)[C:23]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CNOC>CN(C)C=O.O>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:19]([O:28][CH3:29])[CH3:23])=[O:5]
To a solution of 2,6-dichloronicotinic acid (500 mg, 2.63 mmol, Aldrich 90%) in anhydrous N,N-dimethylformamide (5 mL) were added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.28 g, 3.37 mmol, Aldrich), 1-hydroxybenzotriazole hydrate (456 mg, 3.37 mmol, Aldrich) followed by N,N-diisopropylethylamine (1.3 g, 10.0 mmol) and N,O-dimethylhydroxylamine hydrochloride (306 mg, 3.15 mmol, Aldrich) at 0° C. The reaction was stirred for 1-2 hrs, treated with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated. The crude product was purified on silica gel with hexanes/ethyl acetate to give 2,6-Dichloro-N-methoxy-N-methyl-nicotinamide as a white solid (304.5 mg, 50% yield). HRMS, observed: 233.9968, Calcd for M+: 233.9963
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