Diisopropylamine → HCID 71136229, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4, 1 g, 3.9 mmol, 1.0 equiv), (E)-prop-1-enylboronic acid (0.5 g, 5.9 mmol, 1.5 equiv), diisopropylamine (1.1 ml, 7.8 mmol, 2 equiv), triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt hydrate (0.27 g, 0.43 mmol, 0.11 equiv), and Pd(OAc)2 (44 mg, 0.197 mmol, 0.05 quiv) were dissolved in DMF (9.85 mL)/water (3.28 mL), placed in a sealed tube and heated to 100° C. for 18 h. Following this duration, LCMS showed complete consumption of 1-4. The contents were filtered through Celite and washed with ethyl acetate (10 mL). The filtrate was diluted with saturated NaHCO3 (50 mL) and the layers were separated. The aqueous layer was back-extracted with ethyl acetate (3×20 mL) and the combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a brown semi-solid. Purification by normal-phase HPLC (0-40% EtOAc:hexane) afforded 33-1 as a yellow solid. MS m/z (M+H): observed=260.1.

Provenance & Evidence