1,2-Dibromo-3-methylbenzene → N-(3-bromo-5-methylphenyl)-N'-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine

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Reaction Conditions

Reaction Steps

A dry 250 mL 3-necked flask was charged with Pd2(dba)3 (266 mg, 2 mol %), BINAP, 384 mg, 4 mol %), and sodium t-butoxide (2.2 g, 0.023 mol) in 50 mL dry toluene. After 5 minutes, 23A cis-N,N′-bis(7-chloroquinolin-4-yl)cyclohexane-1,4-diamine (4.00 g, 0.0145 mol) was added in one portion followed by dibromotoluene (3.6 g, 0.0145 mol). The solution was heated at 70° C. under nitrogen overnight. The contents were filtered, concentrated and the residue was purified by flash chromatography (5% methanol in dichloromethane) to provide 1.03 g, a 16% yield. MS (ESI(+)Q1MS m/z 445 (M+2 H)+; 1 H NMR (300 MHz, MeOH) δ ppm 8.51 (d, 1 H), 8.37 (d, 1 H), 7.86 (d, 1 H), 7.69 (dd, 1 H), 6.96 (d, 1 H), 6.66 (s, 1 H), 6.61 (s, 1 H), 6.49 (s, 1 H), 3.98 (m, 1 H), 3.63 (m, 1 H), 2.22 (s, 3 H), 1.85-2.01 (m, 8 H).

Provenance & Evidence