Allyltributylstannane → HCID 68630168, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trifluoro-methanesulfonic acid 2-methoxy-quinolin-8-yl ester (3.07 g, 10 mmol, prepared according to WO 2006/021448), allyltributylstannane (3.8 mL, 1.25 eq.), Pd(PPh3)4 (0.29 g, 0.025 eq.) and LiCl (1.6 g, 3.75 eq.) in DMF (20 mL) was stirred at 100° C. for 3 h. After cooling to rt, the mixture was poured on water and extracted with EA. The aq. layer was extracted once more with EA and the combined org. layers were washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 9:1) to give 8-allyl-2-methoxy-quinoline which was contaminated with stannane residues. This crude oil was dihydroxylated following General Method F using AD-mix β, was affording, after purification by CC (Hept/EA 2:1, 1:1, EA) a colourless solid (2.04 g, 87% yield).

Provenance & Evidence