Cesium carbonate → HCID 66977505, compound

Participants

Reaction Steps

A solution of Example 23 step a (430 mg, 1.5 mmol), tert-butyl 2-(4-hydroxyphenyl)acetate (WO2008/024746, 621 mg, 3 mmol), cesium carbonate (978 mg, 3 mmol), copper (I) chloride (74 mg, 0.75 mmol) and 2,2,6,6-tetramethylheptanedione (28 mg, 0.15 mmol) in N-methylpyrrolidinone (2 mL) was heated at 115° C. for 1 h. The reaction mixture was left to cool to RT, diluted with diethyl ether and washed with water. The aqueous layer was extracted with EtOAc and DCM and the combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The resulting oil was purified on a SCX-2 cartridge eluting with EtOAc, MeOH then 1N ammonia in MeOH. The ammonia fractions were concentrated in vacuo and purified twice by FCC (DCM/MeOH containing NH3 10/0 to 9/1 then EtOAc) to provide the title compound as an orange gum (44 mg, 8%). LCMS (Method 8): Rt 4.30 min, m/z 368 [MH+].

Provenance & Evidence