8-Aminoquinoline → N-quinolin-8-ylquinolin-6-amine

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Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 8-aminoquinoline (4.2 grams, 29.0 mmoles), 6-bromoquinoline (6.0 grams, 29.0 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.4 grams, 0.48 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.6 grams, 0.60 mmoles), sodium tert-butoxide (4.7 grams, 49.0 mmoles) and anhydrous toluene (80 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (60 mL) and ethyl acetate (60 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 4.4 grams of the desired product as a yellow solid. 1H NMR (CDCl3) δ 8.8 (d, 2H), 8.6 (bs, 1H), 8.0-8.2 (m, 3H), 7.2-7.8 (m, 7H).

Provenance & Evidence