Diisopropylamine → HCID 19002844, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 5-methylthieno[3,2-b]pyridine (3.60 g, 24 mmol) and N,N-diisopropylamine (100 uL) in THF (80 mL) at -78° C. was added dropwise 16 mL of n-BuLi (1.6M, 25.6 mmol). The mixture was stirred at -78° C. for 20 min and then transfered via a cannula to a solution of N-chlorosuccinimide (4.5 g, 34 mmol) in THF (300 mL) at -10° C. The mixture was stirred at -10° C. for 30 min. Saturated NH4Cl solution was then added and the product was extracted with EtOAc, dried over MgSO4, and concentrated to an oil. Chromatography of the crude oil on silica gel (eluted with 15% EtOAc in hexane) yielded 3.60 g (81%) of the title compound.

Provenance & Evidence