8-Aminoquinoline → HCID 57589728, compound

Participants

Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 8-aminoquinoline (6.81 grams, 47.2 mmoles), 2-bromonapthalene (9.58 grams, 46.3 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.84 grams, 0.92 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.6 grams, 0.92 mmoles), sodium tert-butoxide (8.86 grams, 92.2 mmoles) and anhydrous toluene (90 mL). The contents of the flask were refluxed for sixteen hours; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (135 mL). The combined organic layers were concentrated in vacuo to yield a yellow solid. The solid was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 6.6 grams of the desired product as a yellow solid. 1H NMR (CDCl3) δ 8.75 (d, 1H), 8.4 (bs, 1H), 8.05 (d, 1H), 7.6-7.9 (m, 5H), 7.25-7.5 (m,5H), 7.2 (d, 1H).

Provenance & Evidence