Dimethylformamide → 6-Methoxypyridine-3-carbaldehyde

A solution of n-butyllithium (3.46 mL of a 1.6 M solution in hexanes) in THF (18 mL) was cooled to −78° C. and treated with a solution of 5-bromo-2-methoxypyridine (Johnson, C. R.; Sirisoma, N. S. Tetrahedron Lett. 1998, 39, 2059) 18-1 (1.04 g, 5.53 mmol) in THF (2 mL). The heterogeneous mixture was stirred for 40 min and neat DMF (1.5 mL) was added. The solution was stirred for 90 min at −78° C. and quenched with satd aq NH4Cl solution (2 mL). The cold bath was removed and the mixture warmed to room temperature. The mixture was extracted with EtOAc (2×30 mL) and the combined organic solutions washed with brine, dried over MgSO4, filtered, and concentrated to the desired aldehyde 18-2.

1. stirringThe solution was stirred for 90 min at −78° C.
2. customquenched with satd aq NH4Cl solution (2 mL)
3. customThe cold bath was removed
4. extractionThe mixture was extracted with EtOAc (2×30 mL)
5. washthe combined organic solutions washed with brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated to the desired aldehyde 18-2

ORD record

ord-f026408c168641f6b65d0cde99006b84

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06297249B1