Potassium Phosphate, Tribasic → HCID 52931853, compound

Participants

Reaction Steps

1-(4-Bromo-2-chlorobenzyl)-3-ethylimidazolidine-2,4-dione (2C5) (0.106 mmol, 35 mg), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (1A5) (106 mmol, 31.6 mg), tris(dibenzylidineacetone)dipalladium (0.005 mmol, 4.8 mg), tricyclohexylphosphine (0.013 mmol, 3.6 mg) and potassium phosphate (0.317 mmol, 67 mg) were dissolved in dioxane (2 ml) and water (1 ml) and the mixture was heated at 120° C. in the microwave for 30 min. The sample was concentrated and partitioned between DCM and water and the organic layer collected and dried using a hydrophobic fritted tube before concentration. Purification using basic semi-prep HPLC afforded 1-(2-chloro-4-(2-cyclopropyl-1-oxoisoindolin-5-yl)benzyl)-3-ethylimidazolidine-2,4-dione (Example 2a) 15.1 mg (33%); 1H NMR (400 MHz, CDCl3) δ 7.90 (d, 1H) 7.62 (m, 2H) 7.56 (s, 1H) 7.51 (d, 1H) 7.43 (d, 1H) 4.76 (s, 2H) 4.39 (s, 2H) 3.85 (s, 2H) 3.61 (q, 2H) 2.98 (m, 1H) 1.25 (t, 3H) 0.96-89 (m, 4H); LCMS m/z (M+H) 424.0.

Provenance & Evidence