Tricyclohexylphosphine → HCID 68754973, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromoimidazo[1,2-b]pyridazine (53 mg, 0.27 mmol), 9H-fluoren-9-ylmethyl[(1S,2R)-2-({[5-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (187 mg, 0.294 mmol), Pd2(dba)3 (25 mg, 0.03 mmol), tricyclohexylphosphine (19 mg, 0.07 mmol), and aqueous tribasic potassium acetate (0.71 mL, 0.91 mmol, 1.27 M) were placed into a sealed tube and 1,4-dioxane (5.4 mL) added. The sealed tube was purged with nitrogen for 5 minutes and heated at 100° C. for 18 h. The solution was cooled to room temperature and additional 9H-fluoren-9-ylmethyl[(1S,2R)-2-({[5-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl]carbonyl}amino)-3,3-difluorocyclohexyl]carbamate (85 mg, 0.13 mmol), Pd2(dba)3 (12 mg, 0.01 mmol), tricyclohexylphosphine (8 mg, 0.03 mmol), and aqueous tribasic potassium acetate (0.42 mL, 0.54 mmol, 1.27 M) were added. The sealed tube was purged with nitrogen for 5 minutes and heat at 100° C. for 4 h. The solution was then cooled to room temperature and quenched with aqueous saturated sodium bicarbonate and extracted with dichloromethane (×3). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was taken on to the deprotection step without purification. LRMS (APCI) calc'd for (C34H31F2N5O3S) [M+H]+, 628.2. found 628.2.

Provenance & Evidence