Potassium Acetate → {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid

Temperature

90 °C

N-(5-Bromo-2-chloro-3-pyridinyl)methanesulfonamide (5 g, 17.51 mmol), potassium acetate (5.16 g, 52.5 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (4.89 g, 19.26 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (1.281 g, 1.751 mmol) were placed in 1,4-dioxane (51 ml) and the mixture heated for 16 h at 90° C. The reaction was left stirring at 90° C. for a further 5 h. Further catalyst (0.3 g), potassium acetate (1.7 g) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (1.5 g) were added and the mixture stirred at 95° C. overnight. The mixture was cooled to room temperature then the mixture was filtered through a hydrophobic frit and the solvent removed in vacuo. The residue was partitioned between water (250 ml) and dichloromethane (250 ml). the organic layer was collected and the solvent removed in vacuo. The residue was columned on silica (3×100 g) cartridges eluting with 0-25% methanol in dichloromethane over 40 mins gave the title compound as a dark brown oil (4.9 g).

1. waitThe reaction was left
2. stirringthe mixture stirred at 95° C. overnight
3. temperatureThe mixture was cooled to room temperature
4. filtrationthe mixture was filtered through a hydrophobic frit
5. customthe solvent removed in vacuo
6. customThe residue was partitioned between water (250 ml) and dichloromethane (250 ml)
7. customthe organic layer was collected
8. customthe solvent removed in vacuo
9. washeluting with 0-25% methanol in dichloromethane over 40 mins

ORD record

ord-82e7ad5be2de4aa788c29886c0801d9c

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524751B2