Potassium Phosphate, Tribasic → HCID 52932327, compound

Participants

Reaction Steps

2-Cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (1A5) (0.204 mmol, 60.9 mg) was mixed with (R)-3-(4-bromobenzyl)-5-methyloxazolidin-2-one (5F3) (0.185 mmol, 50 mg), tricyclohexylphosphine (0.022 mmol, 8.5 mg), tris(dibenzylidineacetone) dipalladium (0.009 mmol, 8.5 mg) and potassium phosphate (0.315 mmol, 66.7 mg) in dioxane (1mI) and water (0.5 ml). The mixture was heated to 130° C. for 10 minutes in the microwave before addition of DCM (3 ml) and water (2 ml). The phases were mixed and the organic phase collected using a hydrophobic fritted tube and concentrated under reduced pressure. Purification was achieved using basic HPLC to afford (R)-3-(4-(2-cyclopropyl-1-oxoisoindolin-5-yl)benzyl)-5-methyloxazolid in-2-one (Example 5a) 24.1 mg (36%); 1H NMR (400 MHz, CDCl3) δ 7.88 (d, 1H) 7.66 (d, 1H) 7.59 (m, 3H) 7.38 (d, 2H) 4.64 (m, 1H) 4.51-4.41 (m, 2H) 4.37 (s, 2H) 3.54 (m, 1H) 3.03 (m, 1H) 2.97 (m, 1H) 1.43 (d, 3H) 0.95-0.89 (m, 4H) m/z (M+H) 363.2.

Provenance & Evidence