Acetonitrile → 3-(3-Chloropyridin-4-yl)-3-oxopropanenitrile

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A 2.5 M hexane solution of BuLi (16.79 mL, 42.0 mmol) was added dropwise to a solution of diisopropylamine (6.23 mL, 43.7 mmol) in THF (150 mL) at −78° C. The mixture was stirred at 0° C. for 15 min and cooled to −78° C. Acetonitrile (2.192 mL, 42.0 mmol) was added dropwise. The solution gradually turned to milky white. After 1 h at −78° C., methyl 3-chloroisonicotinate (3.00 g, 17.48 mmol) in THF (10 mL) was added dropwise. The flask was rinsed with THF (2 mL) and added. After 1 h at −78° C., the mixture was quenched with brine (200 mL) and acidified to pH˜1. THF was evaporated in vacuo. The aqueous residue was extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4) and concentrated to give impure 3-(3-chloropyridin-4-yl)-3-oxopropanenitrile as a tan solid (3.12 g, 81% pure, 80% yield). MS (ES+) m/z: 181 (M+H); LC retention time: 1.90 min (analytical HPLC Method A).

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