Sodium Carbonate → HCID 54747876, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl N-{[1-(3-bromobenzyl)-4-hydroxy-2-oxo-6-pent-4-enoyl-2,5,6,7-tetrahydro-1H-pyrrolo[3,4-b]pyridin-3-yl]carbonyl}glycinate (50 mg, 0.09 mmol, prepared in similar fashion to Intermediate 5 (compound 5-1) was dissolved in DMA (2 mL) in a 10 mL reaction tube of a CEM Corporation Discover 300 Watt microwave reactor. Aqueaous Na2CO3 (2 M, 0.8 mL, 1.6 mmol), phenylboronic acid (20 mg, 0.16 mmol) and bis(triphenylphosphine)palladium(II) chloride (7 mg, 0.009 mmol) were added and the tube was purged with nitrogen, capped and inserted into the microwave reactor and heated at 115° C., for 15 min. The reaction was diluted with EtOAc, washed with 2 M HCl, dried (Na2SO4), filtered and concentrated. The residue was purified on a C-18 reverse phase chromatography column eluted with 0-100% MeCN in water. The desired fractions were concentrated, diluted with EtOAc and washed with 2 M HCl. The organic portion was isolated, dried (Na2SO4), filtered and concentrated affording the title compound, E43-1. HPLC/MS: 501.9 (M+1); Rt=3.22 min.

Provenance & Evidence