Methyl iodide → HCID 86683441, compound

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[N:23][C:24]#[N:25])[N:14]([C:15]4[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:5]=3[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:28])[C:13](=[N:23][C:24]#[N:25])[N:14]([C:15]4[CH:16]=[N:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

Procedure

To a solution of N-(8-bromo-1-(6-methoxypyridin-3-yl)-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (compound of step 4, 0.674 mmol) in 5 ml of dry DMF at 0° C. was added NaH (60% dispersed in mineral oil, 1.011 mmol). The reaction mixture was stirred for 15 minutes followed by addition of methyl iodide (1.011 mmol). Reaction mixture was stirred at 0° C. for another 1 h and quenched with water. The solvent was removed; aqueous layer was extracted with DCM. Organic layer was dried over anhydrous Na2SO4, concentrated under vacuum and purified (silica gel column, MeOH/CHCl3 as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 9.27 (s, 1H), 8.62 (d, J=3 Hz, 1H), 8.37 (d, J=1.8 Hz, 1H), 8.18 (dd, J=9 Hz, 3 Hz, 1H), 8.08 (d, J=9 Hz, 1H), 7.80 (dd, J=9 Hz, 3 Hz, 1H), 7.21 (d, J=9 Hz, 1H), 7.03 (d, J=3 Hz, 1H), 4.01 (s, 3H), 3.83 (s, 3H); MS (m/z): 409 (M+1)+.