Sodium hydride → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester

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Reaction Steps

105 mg (4.16 mmol) NaH (96%) were added to a solution of 5-(2-Methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester in 50 mL absolute DMF and the mixture was stirred for 30 min. at room temperature. 1.05 g (3.78 mmol) 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole were added and the the mixture and stirring was continued for 3 h. After addition of 21 mg (0.832 mmol) NaH (96%) and 210 mg (0.756 mmol) 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole and standing overnight the mixture was concentrated in vacuo. The residue was dissolved in CH2Cl2 and the solution washed with saturated NaHCO3 solution. The solvent was removed in vacuo and the residue purified by flash chromatography over silica gel using n-heptane/ethyl acetate=3/2 as solvent. The fractions containing the product were concentrated.

Provenance & Evidence