Allyltributylstannane → 8-Allyl-7-chloro-2-methoxy-[1,5]naphthyridine

Participants

Reaction Conditions

Reaction Steps

A flask charged with trifluoromethanesulfonic acid 3-chloro-6-methoxy-[1,5]naphthyridin-4-yl ester (1.50 g; prepared according to WO 2004/058144), allyltributylstannane (1.68 g) and DMF was degassed with N2. The reaction mixture was treated with LiCl (695 mg) and Pd(PPh3)4 (126 mg) and further stirred at 100° C. for 4 h. After cooling, the mixture was poured into 10% aq. NH4OH and EA, the aq. layer was extracted with EA and the combined org. layers were washed with water (2×) and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 4:1), affording a yellow oil (795 mg; 77% yield).

Provenance & Evidence