Pyridine → 3-(3-Bromo-5-chlorophenoxy)-4-methylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-(3-bromo-5-chlorophenoxy)-4-methylpyridine-2-carboxylic acid (11-3; 2 g, 5.84 mmol) in THF (12 mL) was added triethylamine (1.627 mL, 11.68 mmol), pyridine (944 μL, 11.68 mmol), t-butanol (2.79 mL, 29.2 mmol) and diphenylphosphoryl azide (1.89 mL, 8.76 mmol) and the mixture heated to 65° C. for 35 minutes. After this time, the reaction mixture was diluted with CH2Cl2 (2×100 mL) and washed with water (100 mL). The combined organic extracts were concentrated to an oil on a rotary evaporator. This residue was dissolved in trifluoroacetic acid (20 mL) and allowed to stand for 15 minutes. After this time, the solvent was removed in vacuo and the residue was partitioned between CH2Cl2 (2×100 mL) and saturated aqueous NaHCO3 (50 mL). The combined extracts were concentrated on the rotary evaporator and the residue was purified using a RediSep column (330 g) eluting with a gradient of 0-30% EtOAc/CH2Cl2 to give the title compound. LRMS (M+1)=314.9.

Provenance & Evidence