Ammonia → HCID 66604891, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial containing 7-amino-2-bromo-5H-pyrido[3,2-b]indole-4-carboxamide (150 mg, 0.393 mmol), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine (238 mg, 0.787 mmol), PdCl2(dppf)-CH2Cl2 adduct (32 mg, 0.039 mmol) was flushed with nitrogen. DME (2 mL) and Na2CO3 (0.98 mL, 2.0 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 7-amino-2-(4-(morpholinomethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxamide (90 mg, 0.20 mmol, 51% yield) as a yellow solid. MS (ESI) m/z 402.16 (M+H); HPLC retention time of 0.87 min with Xbridge S10 4.6×50 mm column, 3 min gradient, 0-100% B, 4 mL/min. Solvent A: 95% MeOH—5% H2O—0.1% TFA; Solvent B: 5% MeOH—95% H2O—0.1% TFA.

Provenance & Evidence