Trimethyl borate → HCID 58557409, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (0.274 g, 0.841 mmol), tricyclohexylphosphine (20 wt % solution in toluene, 0.094 g, 0.067 mmol), Pd2(dba)3 (0.039 g, 0.042 mmol) and trimethylborate (0.069 g, 0.547 mmol) were added to a solution of N-((1S,3R,4S)-3-ethyl-4-(8-iodo-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-N-((2-(trimethylsilyl)ethoxy)methyl)cyclopropanesulfonamide (0.32 g, 0.421 mmol, prepared using KK from Preparation #GGG.1) in 1,4-dioxane (8 mL). The mixture was degassed and heated at about 85° C. for about 2 h. The solvent was removed and the residue was partitioned between EtOAc and water (20 mL each). The organic phase was washed with brine (15 mL), dried over anhydrous MgSO4, filtered and concd. The resulting mixture was purified by silica gel flash chromatography (40 to 100% of EtOAc in heptane) to yield N-((1S,3R,4S)-3-ethyl-4-(8-methyl-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-N-((2-(trimethylsilyl)ethoxy)methyl)cyclopropanesulfonamide (0.21 g, 77%) as a yellow amorphous solid. LC/MS (Table 1, Method a) Rt=3.39 min; MS m/z: 650 (M+H)+.

Provenance & Evidence