Toluene → 8-(1,1-Dioxidothiomorpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]-phthalazin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vial was charged with the 8-chloro-2-(2-(quinolin-2-yl)ethyl)phthalazin-1(2H)-one from Example 98.4 (100 mg, 0.30 mmol), Cs2CO3 (194 mg, 0.59 mmol), Pd2(dba)3 (5.45 mg, 5.96 μmol) and BINAP (11.13 mg, 0.018 mmol). The solids were purged with argon for 1 h. A separate flask was charged with toluene (993 μl) and thiomorpholin 1,1-dioxide (48.3 mg, 0.36 mmol), degas with argon for 1 h and then transferred to the microwave reaction vial under inert conditions. The resulting reaction mixture was heated on microwave at 100° C. for 20 h. The reaction mixture was poured into water and extracted with DCM. The solids were removed. The organic layer was washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on a silica column (eluent: DCM/methanol) and then recrystallized from EA to afford the title product (87 mg, 67.2%).

Provenance & Evidence