3-Chloro-4-fluoroaniline → HCID 57580568, compound

Participants

Reaction Steps

A solution of 2-(4-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethoxymethyl)-morpholine-4-carboxylic acid tert-butyl ester (60 mg, 0.15 mmol) in CH2Cl2 (3 mL) was cooled to 0 C. and treated with a solution of mCPBA (56 mg, 0.32 mmol) in CH2Cl2 (2 mL). The reaction was stirred for 15 minutes at 0 C. then warmed to room temperature. To this solution was added 3-chloro-4-fluoroaniline and stirred at room temperature for one hour. The resulting orange solution was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3, then saturated aqueous NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. Preparative reverse-phase HPLC afforded the desired compound (30 mg, 41%). HPLC tR=4.383 min (YMC S5 ODS 4.6×50 mm, 10–90% aqueous methanol, 4 min gradient, monitored at 220 nm). LC/MS (M+H)=492.

Provenance & Evidence