Potassium Carbonate → HCID 58387138, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL Biotage™ microwave vial was charged with 6-chloro-5-iodo-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (Intermediate 5, 73.2 mg, 0.150 mmol), 4-(2H-pyrazol-3-yl)-phenylboronic acid (33.9 mg, 0.180 mmol) and Pd(PPh3)4 (8.7 mg, 5 mol %) followed by dioxane (1.5 mL) and 1M aqueous K2CO3 (180 uL). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 130° C. for 10 min. The suspension was then diluted with EtOAc (5 mL) and washed with 1M aqueous K2CO3 (twice, 1 mL) and water (twice, 1 mL). The organic layer was evaporated to dryness in vacuo to give yellow oil. The oil was dissolved in ACN and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The solvent was evaporated to dryness in vacuo to give the crude product as pale yellow solid. LR-MS (API-ES): calculated for C23H27ClN4O3SSi 502.1, observed m/e 503.0 (M+H)+ (Rt 3.30 min).

Provenance & Evidence