Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-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 → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-cyano-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-(tert-butoxy)-2-[(22S)-5,8-dibromo-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 (50 mg, 0.061 mmol, 1.0 equiv) was placed in a microwave tube, followed by zinc (0.401 mg, 6.13 μmol, 0.1 equiv), dicyanozinc (14.40 mg, 0.123 mmol, 2.0 equiv), and Pd(dppf)Cl2 (50.1 mg, 0.061 mmol, 1.0 equiv). To this mixture was added DMAC (681 μl) and degassed, sealed, placed in microwave, and stirred for 2 hours at 150° C. Then it was diluted by 10 mL EA, washed by NaHCO3, dried over MgSO4, concentrated to give the pure enough product. LCMS (ESI, M+1): 683.4.

Provenance & Evidence