Dimethylformamide → 1-(4-Fluorophenyl)-4-hydroxymethyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

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Reaction Steps

To a solution of 1-(4-fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrole, 5, (in FIG. 6) (prepared as described in J. Med. Chem., 1997, 40, 1619) (1 mmol) in dry DMF (10 mL) at 0° C. is added phosphorus oxychloride (1 mmol). The reaction is monitored by tlc and when it is complete, the mixture is poured onto ice and made basic with aqueous sodium hydroxide. The product is isolated by extraction with CH2Cl2. The extract is dried and evaporated to afford a residue. To the residue, dissolved in EtOH (10 mL) is added sodium borohydride (100 mg). After one hour, the solution is added to water and extracted with ethyl acetate. The extract is washed with dilute HCl, dried and evaporated. The title compound 6 is purified and isolated by HPLC.

Provenance & Evidence