2-Chloro-5-fluorobenzeneboronic acid → Tert-butyl n-(3-{5-[2'-chloro-5'-fluoro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-n-methylglycinate

Participants

Reaction Steps

Tert-butyl N-(3-{5-[2′-chloro-5′-fluoro-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate was prepared following the general procedure 11 starting from Intermediate 41 and 2-chloro-5-fluorophenylboronic acid (Combiblocks BB-2251). After purification by flash chromatography (silica, cHex/EtOAc), the ester derivative was deprotected following the general procedure 8. After purification by precipitation from ACN, the title compound was obtained as a white powder. HPLC (Method A), Rt 4 min (purity: 97.1%). LC/MS (Method B): 494.1 (M−H)−, 495.9 (M+H)+. Elemental analysis: [C26H23N3O4ClF—HCl-0.25H20] Corrected: C, 58.16%; H, 4.60%; N, 7.83%; Cl, 13.21%. Found: C, 58.18%; H, 4.61%; N, 7.77%; Cl, 13.23%. 1H NMR (DMSO-d6, 300 MHz) δ 8.35 (m, 2H), 8.22 (m, 2H), 7.81 (d, J=7.8 Hz, 1H), 7.75-7.67 (m, 2H), 7.52 (d, J=8.0 Hz, 1H), 7.43-7.33 (m, 2H), 4.50 (s, 2H), 4.32 (d, J=13.1 Hz, 1H), 4.27 (d, J=13.1 Hz, 1H), 4.11 (s, 2H), 3.27 (s, 3H), 2.81 (s, 3H).

Provenance & Evidence