Ammonia → HCID 66604967, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-7-(3-oxomorpholino)-5H-pyrido[3,2-b]indole-4-carboxamide (30 mg, 0.077 mmol), 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholine (48 mg, 0.15 mmol), PdCl2(dppf)-CH2Cl2 adduct (6 mg, 8 μmol) was flushed with nitrogen. DME (1.5 mL) and Na2CO3 (0.19 mL, 0.39 mmol, 2.0 N aq. solution) were added and the vial was sealed and heated at 100° C. for 2 hrs. This was diluted with DMF and preparative HPLC (100×30 mm Luna C18 column, Solvent A=10% Methanol, 90% H2O, 0.1% TFA; Solvent B=90% Methanol, 10% H2O, 0.1% TFA, 10-60% B at 42 mL/min over 20 min) followed by SCX capture and release with 2 N NH3 in MeOH afforded 2-(5-(morpholinomethyl)thiophen-2-yl)-7-(3-oxomorpholino)-5H-pyrido[3,2-b]indole-4-carboxamide (23 mg, 0.046 mmol, 60% yield) as a yellow solid. MS (ESI) m/z 492.15 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.67 (1H, s), 8.54 (1H, s), 8.37 (1H, s), 8.20 (1H, d, J=8.24 Hz), 7.92(1H, s), 7.74 (1H, d, J=1.83 Hz), 7.67 (1H, d, J=3.66 Hz), 7.30 (1H, dd, J=8.24, 1.83 Hz), 7.05 ( 1H, d, J=3.66 Hz), 4.27 (2H, s), 4.01-4.07 (2H, m), 3.79-3.88 (2H, m), 3.73 (2H, s), 3.63 (4H, t, J=4.73 Hz), 2.47 (4H, br. s.).

Provenance & Evidence