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Zinc (15.97 g, 244.0 mmol) was suspended in acetic acid (240 ml) and cooled to 0C. Solid 2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylethenamine (5.56 g, 24.42 mmol) was added portion- wise over about 5 minutes and then the reaction mixture was placed under an atmosphere of argon. The reaction was stirred for 18 h, after which time LCMS analysis indicated that the reaction was complete. The mixture was filtered through Celite, washing with EtOAc. The filtrate was concentrated to give a brown oil. The reaction mixture was partitioned between EtOAc and IN NaOH. The aqueous layer was extracted with EtOAc (3x) and the combined organic layer was dried over Na2S04, filtered and concentrated. The residue was adsorbed onto silica gel and purified by flash column chromatography on silica gel, eluting with EtOAc/isohexane (0-100%) to give 2.79 g of an off-white solid, that is approximately a 10: 1 mixture of the title compound along with 5-methoxy-lH-pyrrolo[2,3-c]pyridine as a minor impurity. The mixture was taken forward into the next step as is. LRMS (ESI) calc'd for (C7H5C1N2) [M+H]+, 153; found 153
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