Sodium Carbonate → HCID 66604781, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial containing a mixture of 2-bromo-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (50 mg, 0.13 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (54 mg, 0.26 mmol), PdCl2(dppf)-CH2Cl2 adduct (11 mg, 0.013 mmol), and 2 N aq. Na2CO3 (0.32 mL, 0.64 mmol) was flushed with nitrogen. DME (5 mL) was added and the vial was sealed and heated at 100 ° C. in an oil bath for 2 hrs. The reaction was diluted with MeOH, filtered, and the solid was washed with MeOH. The solvents were removed from the combined filtrates and preparative HPLC (PHENOMENEX® Luna C18 30×100 10u Column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; 30 to 100% B over 20 min at 30 mL/min. SCX capture and release with 2 N NH3 in MeOH gave 2-(1-methyl-1H-pyrazol-4-yl)-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxamide (27 mg, 0.066 mmol, 51% yield) as a yellow solid. MS (ESI) m/z 401.27 (M+H). 1H NMR (500 MHz, acetone) d ppm 10.66 (1H, br. s.), 9.34 (1H, d, J=1.83 Hz), 8.50 (1H, dd, J=8.09, 2.29 Hz), 8.32 (1H, s), 8.16 (1H, d, J=8.85 Hz), 8.11 (1H, br. s.), 7.36 (1H, d, J=8.24 Hz), 7.30 (1H, d, J=1.83 Hz), 7.12 (1H, br. s.), 7.08 (1H, dd, J=8.70, 2.29 Hz), 3.33-3.40 (4H, m), 2.78 (4H, br. s.), 2.57 (3H, s), 2.31 (3H, s).

Provenance & Evidence