Toluene → HCID 178430464, compound

Participants

Reaction Steps

Trans-4-(4-Bromo-3-chloro-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 155, 100 mg, 0.193 mmol), Pd tetrakis (45 mg, 0.039 mmol), Na2CO3 (52 mg, 4.83 mmol) and 2-methyl-4-pyridine boronic acid (34 mg, 0.251 mmol) was dissolved in EtOH (4 ml) and toluene (4 ml) under N2 and the mixture was refluxed overnight. LCMS indicated that the reaction was complete, and it was concentrated in vacuo. then taken up in EtOAc and washed with H2O (×2). The organic layer was concentrated in vacuo, and the crude material was purified via column chromatography using a biotage SP1 25+S column with a gradient 80%-100% EtOAc in heptane. Product fractions were combined and repurified on prep-HPLC (150 mm, C8 luna, 15-20 min run, 10%-100% MeCN in water containing 0.1% TFA), then lyophilized to yield the title compound as a white solid (27 mg, 22%). MS MH+ 530.1

Provenance & Evidence