Cesium carbonate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-ethenyl-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

Participants

Reaction Conditions

Reaction Steps

Methyl(2S)-2-[(22S)-5-bromo-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]-2-(tert-butoxy)acetate (40 mg, 0.054 mmol, 1.0 equiv), potassium trifluoro(vinyl)borate (36.4 mg, 0.271 mmol, 5 equiv) were mixed in DMF (1.0 mL) and water (0.10 mL). To this solution was added Pd(OAc)2 (1.21 mg, 0.005 mmol, 0.1 equiv), Sphos (4.46 mg, 0.011 mmol, 0.2 equiv) and cesium carbonate (35.4 mg, 0.11 mmol, 2.0 equiv). The solution was degassed by N2 for five minutes. Then it was stirred at 80° C. for 2 hours. The mixture was loaded onto 12 g ISCO column and purified by 0-100% Ethyl Acetate [2% TEA]/Hexane to provide the product (35 mg, 94.3%) as a brown oil. LCMS (ESI, M+1): 684.4.

Provenance & Evidence