Oxalyl chloride → 4-[(4-Fluorophenyl)sulfanyl]aniline

Beteiligte Stoffe

Reaktionsschritte

Oxalyl chloride (1.68 mL, 19.59 mmol) and a catalytic amount of N,N-dimethylformamide are added to a pre-cooled (0° C.) suspension of 2-chloroisonicotinic acid (1.032 g, 6.55 mmol) in dichloromethane (350 mL). After the gas evolution ceases, the mixture is allowed to reach room temperature and is stirred for 1 h. The volatiles are then removed under reduced pressure. The residue obtained is dissolved in dichloromethane (150 mL) and the resulting solution is added to a pre-cooled (0° C.) solution of crude benzyl 5-(4-fluorophenylthio)spiro[indoline-3,4′-piperidine]-1-carboxylate (3.50 g, 42% wt/wt, 3.25 mmol) and N,N-diisopropylethylamine (1.65 mL, 9.64 mmol) in dichloromethane (400 mL). The reaction is stirred for 45 min at room temperature until complete conversion of the starting material is observed. The reaction mixture is washed with saturated aqueous sodium hydrogen carbonate (100 mL) and with brine (100 mL). The organic layer is dried over sodium sulphate, is filtered and is concentrated under reduced pressure. The yellow oil isolated is purified by column chromatography on silica gel (heptane/ethyl acetate 25 to 50% as eluent) to afford the desired product (1.58 g, 2.69 mmol, 83% yield) (HPLC-MS Method 2: retention time: 2.268 min, m/z 588.0).

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