Diiodomethane → Methyl 3-cyclopropylpyridine-2-carboxylate

To a stirred solution of diiodomethane (2.46 g, 9.20 mmol) in dry DCM (5 ml) at −10° C. was added diethyl zinc in hexane (1 M, 9.2 ml, 9.20 mmol). The reaction was stirred for 30 minutes under nitrogen. To this was then added methyl 3-ethenylpyridine-2-carboxylate (0.30 g, 1.84 mmol) as a solution in DCM (5 ml) over a 15 minute period. The reaction was then allowed to warm to room temperature and was stirred at room temperature for 15 hours. The reaction mixture was diluted with a saturated solution of ammonium chloride (25 ml) and the organics were extracted with ethyl acetate (3×30 ml). The combined organics were washed with water (25 ml), brine (25 ml), dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane to afford the title compound.

1. stirringwas stirred at room temperature for 15 hours
2. extractionthe organics were extracted with ethyl acetate (3×30 ml)
3. washThe combined organics were washed with water (25 ml), brine (25 ml)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe resulting residue was purified by column chromatography (silica, 0-15% ethyl acetate/n-hexane

ORD record

ord-492dac1536614cd9a0dc88df3298a9b0

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156829B2