Tributylphenyltin → 2-(3-methoxyphenyl)-9-phenyl-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-iodo-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (Example 30) (250 mg, 0.56 mmol), tributyl(phenyl)stannane (202 μL, 1.10 mmol) and Pd(PPh3)4 (33 mg, 0.03 mmol) in 1,4-dioxane (4 mL) was heated in a microwave reactor at 140° C. for 1 h. The mixture was then filtered and concentrated in vacuo. The crude product obtained was purified by flash chromatography (SiO2, hexane to hexane/AcOEt 3:1) to give a yellow oil that was recrystallized from heptane to afford the title compound (144 mg) as white solid. UPLC-MS: MS 395.1 (M+H+); UPLC rt 1.20 min. 1H NMR (400 MHz, CHLOROFORM-d): δ ppm 2.90 (t, J=6.06 Hz, 2 H); 3.79 (t, J=6.26 Hz, 2 H); 3.86 (s, 3 H); 4.53 (br. s., 2 H); 6.97 (s, 1 H); 6.97-7.04 (m, 1 H); 7.28-7.37 (m, 3 H); 7.37-7.51 (m, 7 H); 7.68 (t, J=4.50 Hz, 1 H).

Provenance & Evidence