Hydrochloric Acid → HCID 68951087, compound

Participants

Reaction Conditions

Reaction Steps

Add 4-chlorophenyl boronic acid (215 mg, 1.38 mmol) to a slurry of 2-iodo-3-methyl-4,5-dihydro-thieno[2,3-c]pyran-7-one (135 mg, 0.46 mmol) in CH3CN (2 mL). Add PPh3 (37 mg, 0.14 mmol) followed by 2.0 M Na2CO3 (0.69 mL). Bubble dry argon through the reaction for 15 min. Add Pd(OAc)2 (12 mg, 0.05 mmol) and heat using microwave irradiation to 100° C. for 45 min. Pour the reaction into 1N HCl (50 mL) and extract with EtOAc (3×50 mL). Wash the combined organic extracts with brine (50 mL). Concentrate, dissolve the crude residue in toluene (5 mL) and treat with p-toluenesulfonic acid monohydrate (50 mg, 0.26 mmol). Heat to 80° C. for 8 h. Cool to RT, pour into aqueous NaHCO3 (50 mL) and extract with EtOAc (3×50 mL). Wash the combined extracts with brine (50 mL) and concentrate. Purify the resulting residue using silica gel chromatography (0-50% EtOAc/hexanes) to provide 111 mg (87%) of the desired product.

Provenance & Evidence