Ammonia → HCID 66604529, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (50 mg, 0.120 mmol), 3-chloro-4-methoxyphenylboronic acid (33.5 mg, 0.180 mmol), PdCl2(dppf)-CH2Cl2 adduct (9.8 mg, 0.012 mmol) in a microwave vial was flushed with nitrogen. DME (2 mL) and aq. Na2CO3 solution (0.30 mL, 0.60 mmol, 2.0 M) were added and the vial was sealed and heated at 100° C. for 3.5 hr. 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 to 70% gradient over 20 min at 42 mL/min) followed by SCX capture and release with 2 N NH3 in MeOH gave 2-(3-chloro-4-methoxyphenyl)-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide (10 mg, 0.023 mmol, 19% yield) as a solid. MS (ESI) m/z 437.21 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 11.24 (1H, s), 8.53 (1H, s), 8.35 (1H, d, J=2.14 Hz), 8.27 (1H, s), 8.24 (1H, dd, J=8.55, 2.14 Hz), 8.08 (1H, d, J=8.85 Hz), 7.82 (1H, s), 7.31 (1H, d, J=8.85 Hz), 7.22 (1H, d, J=2.14 Hz), 7.01 (1H, dd, J=8.55, 2.14 Hz), 3.95 (3H, s), 3.78-3.85 (4H, m), 3.22-3.27 (4H, m).

Provenance & Evidence