1-(azidomethyl)-4-methylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-ethynyl-6-(4-(4-methylpiperazin-1-yl)phenyl)-9H-pyrido[2,3-b]indole (example 44, 26.1 mg, 0.071 mmol) in 1.4 mL of anhydrous DMF (C=0.05M), was added CuI (2 mg, 0.15 eq) and 185 μL of a 0.5M solution of 1-(azidomethyl)-4-methylbenzene (1.3 eq). Then, diisopropylethylamine (82 μL, 7 eq) was introduced. The reaction mixture was stirred at room temperature for 15 h. The mixture was then hydrolysed with water (30 mL) The aqueous layer was extracted with AcOEt (4×15 mL). The combined organic layers were washed twice with brine, dried over MgSO4, filtered and concentrated under reduced pressure. A light brown solid was obtained in 66% yield (24.2 mg) after trituration of the crude product in MeOH and filtration. 1H NMR (500 MHz, DMSO) δ 11.99 (s, 1H), 9.01-8.92 (m, 2H), 8.47 (s, 1H), 7.70 (dd, J=8.4, 1.6 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.49 (d, J=8.7 Hz, 2H), 7.41 (d, J=3.6 Hz, 1H), 7.34 (d, J=7.9 Hz, 2H), 7.19 (d, J=7.8 Hz, 2H), 7.02 (d, J=8.7 Hz, 2H), 5.73 (s, 2H), 3.19 (s, 4H), 2.29 (s, 3H), 2.25 (s, 3H); 13C NMR (126 MHz, DMSO) δ 153.1 (s), 149.5 (s), 145.5 (CH), 144.9 (s), 137.9 (s), 137.3 (s), 132.8 (s), 132.6 (s), 131.6 (s), 131.5 (s), 129.1 (CH), 127.7 (CH), 126.7 (CH), 125.0 (CH), 124.4 (CH), 121.5 (CH), 120.5 (s), 115.5 (CH), 110.9 (CH), 54.4 (2CH2), 52.8 (CH2), 47.9 (2CH2), 45.4 (NCH3), 20.4 (CH3); HRMS calcd for C32H32N7 [M+H]+ 514.2714 found 514.2699. hydrolysed with water (30 mL) The aqueous layer was extracted with AcOEt (4×15 mL) The combined organic layers were washed twice with brine dried over MgSO4 filtered concentrated under reduced pressure A light brown solid was obtained in 66% yield (24.2 mg) after trituration of the crude product in MeOH and filtration