Dimethylformamide → 5-Bromo-2-methoxypyridine-4-carbaldehyde

Temperature

0 °C

To a solution of diisopropylamine in THF (0.1M) at 0° C. was added n-BuLi (1.1 eq.). The solution was stirred for 30 min and then was cannulated in a solution of commercially available 5-bromo-2-methoxypyridine in THF (0.1M) at −78° C. The resulting solution was stirred at −78° C. for 30 min then DMF (1.5 eq.) was added. Final reaction mixture was allowed to warm to 0° C. before it was quenched with saturated aqueous NH4Cl and then extracted with EtOAc. The organic extract was washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 50% in 30 min) afforded the desired compound as a white solid.

1. stirringThe resulting solution was stirred at −78° C. for 30 min
2. customFinal reaction mixture
3. customwas quenched with saturated aqueous NH4Cl
4. extractionextracted with EtOAc
5. extractionThe organic extract
6. washwas washed with saturated NaHCO3, brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
11. washeluting with Hex/EtOAc (0 to 50% in 30 min)

ORD record

ord-53972ecfc5b34bcfbfc82dc1e3960f9d

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334308B2