Triethylamine → HCID 118353193, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled suspension of 6-fluoro-9-hydroxy-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid benzyl ester (170 mg, 0.54 mmol, 1.00 eq) in DCM (10 mL), NEt3 (0.23 mL, 1.62 mmol, 3.00 eq) and trifluoromethanesulfonic anhydride (0.14 mL, 0.81 mmol, 1.50 eq.) were added in sequence. The reaction mixture was stirred at 0° C. for 30 min and further at r.t. for 45 min. The mixture was diluted with DCM (20 mL) and washed with sat. aq. NaHCO3 soln. (2×10 mL). The org. layer was dried over MgSO4 and concentrated in vacuo. To a mixture under N2 of the resulting triflate, [4-methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid ethyl ester (173 mg, 0.54 mmol, 1.00 eq.), and sodium carbonate (229 mg, 2.16 mmol, 4.00 eq.) in toluene/EtOH/water 20:4:1 (10 mL), tetrakis(triphenylphosphine) palladium (0) (31 mg, 0.03 mmol, 0.05 eq.) was added. The mixture was stirred at 100° C. for 17 hours. The mixture was allowed to cool to r.t. and concentrated in vacuo. The residue was taken up in DMF, filtered, and purified by prep. HPLC (column Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give the title compound as a brown oil.

Provenance & Evidence