Potassium Phosphate, Tribasic → HCID 72206279, compound

Participants

Reaction Conditions

Reaction Steps

A degassed mixture of 2-bromo-5-(5-chloro-2-methyl-phenyl)-6-(4-chloro-phenyl)-1-isopropyl-5,6-dihydro-1H-pyrrolo[3,4-b]pyrrol-4-one (Intermediate B) (0.337 mmol), 5-cyano-2-methoxyphenylboronic acid [612833-37-1] (0.675 mmol), Pd(PPh3)4 (0.067 mmol) and K3PO4 (1.350 mmol) in 2:1 dioxane/H2O (4.5 mL) was heated at 100° C. for 4 h. After cooling to rt, the reaction mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic phases were dried (Na2SO4) and concentrated. The residue was dissolved in CH2Cl2 and filtered through a PL-thiol MP SPE cartridge (StratoSpheres), washing through with additional CH2Cl2. The filtrate was re-concentrated and the residue purified using a RediSep® silica gel column to afford the title compound as a yellow solid. tR: 5.43 min (HPLC 1); ESI-MS: tR=1.37 min, [M+H]+ 530/532/534 (LC-MS 1); TLC: Rf=0.29 (1:1 EtOAc/heptanes); 1H-NMR (d6-DMSO, 600 MHz): 8.15 (br s, 1H), 7.95 (m, 1H), 7.77 (m, 2H), 7.37 (m, 2H), 7.31 (d, 1H), 7.24 (m, 1H), 7.15 (m, 1H), 7.10 (m, 1H), 6.51 (s, 1H), 6.31 (s, 1H), 3.85 (m, 1H), 3.85 (s, 3H), 1.91 (s, 3H), 1.29 (m, 3H), 0.46 (m, 3H).

Provenance & Evidence