Potassium Phosphate, Tribasic → HCID 52932398, compound

Participants

Reaction Steps

1-((5-Bromopyridin-2-yl)methyl)-3-methylimidazolidine-2,4-dione (9J5) (0.229 mmol, 65 mg), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (1A5) (0.229 mmol, 68.0 mg), tris(dibenzylidineacetone)dipalladium (0.011 mmol, 10.5 mg), tricyclohexylphosphine (0.027 mMol, 7.7 mg) and potassium phosphate (0.389 mmol, 83.0 mg) were suspended in dioxane (1 ml) and water (0.5 ml) and heated to 130° C. in the microwave for 15 min. The reaction mixture was quenched with 2 ml of water and 3 ml of DCM and then passed through a hydrophobic fritted tube, washing with DCM. The organic layers were concentrated and the residue purified by basic prep HPLC to give 1-((5-(2-cyclopropyl-1-oxoisoindolin-5-yl)pyridin-2-yl)methyl)-3-methylimidazolidine-2,4-dione (Example 9a) 27.6 mg (32.1%); 1H NMR (400 MHz, CDCl3) 8.79 (dd, 1H) 7.91 (m, 2H) 7.64 (dd, 1H) 7.59 (s, 1H) 7.39 (d, 1H) 4.75 (s, 2H) 4.40 (s, 2H) 4.04 (s, 2H) 3.07 (s, 3H) 2.97 (m, 1H) 0.97-0.88 (m, 4H) LCMS m/z (M+H) 377.2.

Provenance & Evidence