Picolinic acid → HCID 70817475, compound

To a stirred solution of 7-bromo-imidazo[1,2-a]pyridine (600 mg, 3.0 mmol) and diethyl malonate (0.93 mL, 6.1 mmol) in dry dioxane (15 mL) was added cesium carbonate (3 gm, 9.1 mmol). Argon was bubbled through the mixture for 10 minutes and then copper (I) iodide (116 mg, 0.61 mmol) and picolinic acid (150 mg, 1.22 mmol) were added. The resultant mixture was heated in a sealed tube at 130° C. for 24 hours. The reaction mixture was cooled to room temperature, quenched with water (10 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (2×10 mL), brine (10 mL), dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with a gradient of dichloromethane:methanol 100:0 to 98:2 to afford the title compound as an off-white gum in 29% yield, 180 mg.

1. customArgon was bubbled through the mixture for 10 minutes
2. customquenched with water (10 mL)
3. extractionextracted with EtOAc (3×20 mL)
4. washThe combined organic layers were washed with water (2×10 mL), brine (10 mL)
5. dry with materialdried over sodium sulphate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude material was purified by silica gel column chromatography
9. washeluting with a gradient of dichloromethane:methanol 100:0 to 98:2

ORD record

ord-5ebf9a2b97784a3b9773f8ee907e85ad

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846698B2