HCID 22025700, compound → HCID 22025669, compound

Participants

Reaction Steps

Methyl 3,4-difluoro-2-[2-fluoro-4-(3-hydroxy-1-propynyl)anilino]benzoate was dissolved in absolute EtOH and hydrogenated in the presence of 5% Pd/C by the general procedure of Example 1, Step D. Purification of the resulting oil was carried out by column chromatography on silica gel (20% EtOAc/PE as eluant) to give methyl 3,4-difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]benzoate as a waxy white solid (93%), used directly in the next step. 1H NMR [400 MHz, (CD3)2SO] δ 8.81 (s, 1 H), 7.78 (ddd, J=9.0, 6.1, 2.0 Hz, 1 H), 7.10-7.02 (m, 2 H), 6.98 (ddd, J=8.3, 8.3, 4.0 Hz, 1 H), 6.94 (dd, J=8.2, 1.9 Hz, 1 H), 4.46 (t, J=4.8 Hz, 1 H), 3.82 (s, 3 H), 3.43-3.37 (m, 2 H), 2.58 (t, J=7.7 Hz, 2 H), 1.74-1.66 (m, 2 H). LCMS (APCI−) 338 (M−H). Step C: Preparation of 3,4-difluoro-2-[2-fluoro-4-(3-hydroxypropyl)anilino]benzoic acid

Provenance & Evidence