Dichloromethane → HCID 59464096, compound

Temperature

80 °C

A stirred solution of 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-7-ene prepared as above (8.40 g, 31.56 mmol), 2-bromo-5-nitropyridine (6.0 g, 29.55 mmol) in DME (200 mL), degassed 2M potassium carbonate (40 mL) was added palladium tetrakis(triphenylphosphine) (Pd(PPh3)4; 1.8 g, 1.58 mmol). The reaction mixture was evacuated with nitrogen (3 cycles) and allowed to stir under vacuum for 5 minutes, then heated to 80° C. overnight. The reaction mixture was allowed to cool to ambient temperature, EtOAc (200 mL) was added followed by water (200 mL), the suspension was filtered and the organic phase was separated and the aqueous layer re-extracted into EtOAc (200 mL). The organic extracts were combined, washed with brine (200 mL), dried (MgSO4) and concentrated to leave crude product. DCM was added and the suspension was filtered and dried to leave the title compound (1.64 g). The filtrate was concentrated after the addition of DCM a further 1.51 g of product was obtained, the filtrate was purified on a 120 g SiliCycle cartridge eluting 20-50-70% EtOAc in isohexane to provide 1.72 g of product. Total yield is 4.85 g (18.51 mmol, 58%);

1. customdegassed 2M potassium carbonate (40 mL)
2. customThe reaction mixture was evacuated with nitrogen (3 cycles)
3. temperatureto cool to ambient temperature
4. additionEtOAc (200 mL) was added
5. filtrationthe suspension was filtered
6. customthe organic phase was separated
7. extractionthe aqueous layer re-extracted into EtOAc (200 mL)
8. washwashed with brine (200 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated
11. customto leave crude product
12. filtrationthe suspension was filtered
13. customdried

ORD record

ord-3bd068e0a7bb44c6bb3b244d8df108c1

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795283B2