Cesium carbonate → HCID 59548547, compound

Participants

Reaction Steps

A mixture of 1-Methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one (273 mg, 0.62 mmol, 1.2 eq), 2-Bromo-6-(8-cyclopropyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-benzaldehyde (200 mg, 0.52 mmol, 1 eq), X-Phos (6 mg, 0.012 mmol, 0.02 eq) Pd(dba)2 (11 mg, 0.019 mmol, 0.03 eq), Cesium carbonate (403 mg, 1.24 mmol, 2 eq) in 7 mL of a 6:1 mixture of dioxane:water was heated to 100 C for 14 hours under argon with stirring. The reaction was cooled, filtered through a sintered glass funnel, concentrated and directly loaded on a silica gel column, eluting with a gradient of 20 to 40% ethyl acetate in hexanes, followed by a gradient of 5 to 10% methanol in CH2Cl2 to give a solid, 383 mg of 2-(8-Cyclopropyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde, 87%.

Provenance & Evidence