Carbazole → HCID 58516589, compound

Participants

Reaction Steps

To 30 mL of dry toluene add 2-iodo-1-(methoxymethoxy)-4-(2,4,4-trimethylpentan-2-yl)benzene (1.50 g, 3.986 mmol), carbazole (0.633 g, 3.786 mmol), K3PO4 (1.71 g, 8.034 mmol), CuI (0.158 g, 0.830 mmol) and trans-N,N-dimethylcyclohexane-1,2-diamine (0.158 g, 1.111 mmol). Reflux the reaction mixture for 48 hours, cool, filter, and concentrate to give material. Purify material by flash chromatography using 3% ethyl acetate in hexanes to give 0.49 g (29.6%) of 9-(2-(methoxymethoxy)-5-(2,4,4-trimethylpentan-2-yl)phenyl)-9H-carbazole as off-white powder. 1H NMR (400 MHz, CDCl3) δ 8.19-8.14 (m, 2H), 7.50-7.25 (m, 7H), 7.19-7.13 (m, 2H), 4.93 (s, 2H), 3.16 (s, 3H), 1.76 (s, 2H), 1.40 (s, 6H), 0.82 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 151.41 (s), 144.96 (s), 141.46 (s), 127.95 (s), 127.19 (s), 126.13 (s), 125.68 (s), 123.11 (s), 120.13 (s), 119.39 (s), 116.20 (s), 110.05 (s), 94.99 (s), 56.99 (s), 56.06 (s), 38.27 (s), 32.40 (s), 31.85 (s), 31.58 (s);

Provenance & Evidence