Methyl iodide → 7-Methoxy-2-methylfuro[2,3-c]pyridine

Temperature

-78 °C

To a solution of 7-methoxyfuro[2,3-c]pyridine (2.9 g, 19.6 mmol) in THF (20 mL) stirred under an atmosphere of argon was added n-BuLi (7.8 mL, 19.6 mmol) at −78° C.; the mixture was transferred to a −30° C. ice bath and was stirred for 2 h. The mixture was cooled to −78° C. and MeI (4.2 g, 29.4 mmol) was added. After the mixture was stirred at rt for 18 h, the reaction mixture was quenched with water (30 mL) and extracted with DCM (50 mL×3). The combined organic layers were washed with brine (30 mL×3), dried over Na2SO4 and concentrated in vacuo to afford the title compound (3.2 g, 100%) as a yellow solid. The material was carried forward without any further purification. LCMS (M+H)+=164.

1. customwas transferred to a −30° C.
2. stirringAfter the mixture was stirred at rt for 18 h
3. customthe reaction mixture was quenched with water (30 mL)
4. extractionextracted with DCM (50 mL×3)
5. washThe combined organic layers were washed with brine (30 mL×3)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-4e9eddf5eae0409d865056791e8790a8

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034900B2