Potassium Phosphate, Tribasic → HCID 136337375, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial containing a mixture of 3-chloro-4-hydroxyphenylboronic acid (64 mg, 0.37 mmol), methyl 2-bromo-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (50 mg, 0.12 mmol), powdered potassium phosphate tribasic (116 mg, 0.546 mmol), 2-dicyclohexylphosphino-2′,4′,6′-tri-iso-propyl-1,1′-biphenyl (12 mg, 0.025 mmol), and Pd(OAc)2 (2.8 mg, 0.012 mmol) was flushed with nitrogen. THF (0.5 mL) was added, the vial was sealed, and the reaction was heated at 80° C. for 3 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; 10-60% B at 42 mL/min over 20 min) of the reaction mixture followed by SCX capture and release with 2 N NH3 in MeOH gave methyl 2-(3-chloro-4-hydroxyphenyl)-7-(4-methylpiperazin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (30 mg, 0.043 mmol, 34.9% yield. MS (ESI) m/z 451.10 (M+H).

Provenance & Evidence