Water → HCID 57856297, compound

Temperature

65 °C

A solution of 2-amino-5-bromo-3-iodopyridine B-78-1 (4.75 g, 15.9 mmol), isopropenylboronic acid pinacol ester (3.28 mL, 2.94 g, 17.5 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]-palladium(II) dichloride dichloromethane complex (1:1) (295 mg, 0.403 mmol) in dimethylformamide (48 mL) was treated with 24 mL of 2.0 M aqueous sodium carbonate solution. The resulting biphasic mixture was stirred under argon in a 65° C. oil bath for 6 hours. After cooling to room temperature, the mixture was diluted with 200 mL ethyl acetate and 75 mL deionized water, then suction-filtered to remove some insoluble black precipitate. After separation, the aqueous layer was back-extracted with 100 mL ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to 5.87 g brown oil. The crude product was purified by silica gel chromatography (eluting with a 10-50% ethyl acetate in hexanes gradient), to give B-78-2 (2.5501 g, 75.3%) as a tan solid.

1. temperatureAfter cooling to room temperature
2. filtrationsuction-filtered
3. customto remove some insoluble black precipitate
4. customAfter separation
5. extractionthe aqueous layer was back-extracted with 100 mL ethyl acetate
6. dry with materialThe combined organic extracts were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated to 5.87 g brown oil
9. customThe crude product was purified by silica gel chromatography (
10. washeluting with a 10-50% ethyl acetate in hexanes gradient),
11. customto give B-78-2 (2.5501 g, 75.3%) as a tan solid

ORD record

ord-0e5ee7ca0c894e648a82b69b44b34f1c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772246B2