3-(2-Chloro-4-nitrophenyl)-4-methylpyridine → 3-Chloro-4-(4-methylpyridin-3-yl)aniline

Participants

Reaction Steps

To a solution of Intermediate 27A (0.136 g, 0.547 mmol) in EtOAc (2.73 mL) was added Pd/C (0.058 g, 0.055 mmol). The mixture was placed under an atmosphere of H2 for 18 hours. The reaction mixture was filtered through CELITE® and the filter cake was washed with CH2Cl2. The solvent was evaporated and the crude material re-dissolved in a minimal amount of CH2Cl2 and chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (40 g column, 1-20% MeOH in CH2Cl2 over 25 min) gave the title compound (0.106 g, 0.485 mmol, 89% yield) as an orange residue. HPLC Ret timej:1.06 min. MS (ES): m/z=219.1 [M+H]+. Intermediate 27 was used in the synthesis of Example 178.

Provenance & Evidence