2-Bromonaphthalene → HCID 58899097, compound

Participants

Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 6-aminoquinoline (6.69 grams, 46.4 mmoles), 2-bromonapthalene (9.15 grams, 44.2 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.80 grams, 0.87 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (1.10 grams, 1.77 mmoles), sodium tert-butoxide (8.49 grams, 88.3 mmoles) and anhydrous toluene (90 mL). The contents of the flask were refluxed for five hours; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with tetrahydrofuran (135 mL). The combined organic layers were concentrated in vacuo to yield a brown solid. The solid was recrystallized from ethanol to afford 8.6 grams of the desired product as a yellow solid. 1H NMR (DMSO-d6/D2O) δ 8.9 (d, 1H), 8.65 (d, 1H), 8.2 (d, 1H), 7.25-8.05 (m, 10H).

Provenance & Evidence