Nitrogen → HCID 11442512, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 12.4 (100 mg, 0.243 mmol) in DMF (1.5 ml) was added tert-butyl acrylate (0.045 ml, 0.304 mmol) and tri-o-tolylphosphine (3.7 mg, 0.0122 mmol). After the 5 min degass with N2, triethylamine (0.068 ml, 0.486 mmol) and Pd(OAc)2 (2.7 mg, 0.0122 mmol) were added, and the reaction mixture stirred at 80° C. for 17 h. Additional reagents (same molar equivalents except triethylamine (0.034 ml, 0.243 mmol) and the mixture was stirred at 100° C. for an additional 3 h. Reagent addition was repeated and the mixture again stirred at 100° C. for 17 h. The solution was partitioned between EtOAc and H2O and the organic phase washed with brine, dried (Na2SO4), concentrated, and the crude product purified by SiO2 chromatography (stepwise gradient: 30 to 50% Et2O/hexanes) to afford 67 mg (60%) of 12.5. MS (ESI) 459.4 (MH+).

Provenance & Evidence