Tributylvinyltin → HCID 90389309, compound

Temperature

80 °C

A sealable vial was charged with methyl 2,5-dichloronicotinate (100 mg, 0.49 mmol, Bionet Research), tributyl(vinyl)stannane (156 μl, 0.53 mmol) and N,N-dimethylformamide (1 mL) at RT under nitrogen atmosphere. 2,6-Ditert-butyl-4-methylphenol (Aldrich, 5 mg) was added, followed by dichlorobis(triphenylphosphine)palladium(II) (Strem, 68 mg, 0.10 mmol) and the reaction mixture was heated to 80° C. for 1 hour. The reaction mixture was cooled to RT and partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was separated and washed with water (2×25 mL) and brine (30 mL), The combined organic layers were dried over anhydrous magnesium sulfate and the filtrate was concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel (5-35% EtOAc/hexanes) to obtain the title compound as a colorless oil (96 mg).

1. temperatureThe reaction mixture was cooled to RT
2. custompartitioned between EtOAc (50 mL) and water (50 mL)
3. customThe organic phase was separated
4. washwashed with water (2×25 mL) and brine (30 mL)
5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe crude product was purified by flash chromatography on silica gel (5-35% EtOAc/hexanes)

ORD record

ord-affa3ad4f0a643d08e385a8b29331321

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2