Toluene → 3-(3-chloro-4-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

3-Bromo-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (33 mg, 0.075 mmol, Example 144A) was dissolved in MeOH (0.6 mL) and added into a microwave vial containing 3-chloro-4-fluorophenylboronic acid (55.7 mg, 0.32 mmol), followed by addition of Na2CO3 (0.12 mL of a 2M aq. solution) and PdCl2(dppf)-CH2Cl2 (6.12 mg, 7.50 μmol) and Toluene (1.2 mL). The vial was sealed and heated in a BIOTAGE® microwave reactor for 15 minutes at 160° C. The reaction mixture was evaporated to dryness, dissolved in DMF+isopropanol and purified by preparative HPLC. Product containing fractions were combined and evaporated to dryness to give 6.0 mg 3-(3-chloro-4-fluorophenyl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide. HPLC retention time 4.72 min. (SUPELCO® Ascentis Express 4.6×50 mm 2.7 um C18, 2 ml/min, 0 to 100% B in 8 minutes, then 100% B for 1 minute. Solvent A: 5% CH3CN—95% H2O—10 mM NH4OAc; Solvent B: 95% CH3CN—5% H2O—10 mM NH4OAc). MS (ESI) m/e+=452 [M+H]+.

Provenance & Evidence