Ethyl bromoacetate → (5-{3-[(2-Chloro-5-methyl-pyrimidin-4-yl)-methyl-amino]-propoxy}-indol-1-yl)-acetic acid ethyl ester

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Reaction Steps

(2-Chloro-5-methyl-pyrimidin-4-yl)-[3-(1H-indol-5-yloxy)-propyl]-methyl-amine (Example 88, 0.117 g, 0.35 mmol) was dissolved in DMF (2 mL) at rt, and sodium hydride was added (0.017 g, 60% in mineral oil, 0.42 mmol). The reaction solution immediately turned purple. The resulting mixture was stirred for 1 h and ethyl bromoacetate (0.065 g, 0.39 mmol) was added. The reaction mixture was stirred for 60 h, diluted with water, and extracted with EtOAc. The organic phases were dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as an orange oil without purification (103 mg, 70%). LC/MS m/z 417.4 (M+H)+, RT 3.05 min.

Provenance & Evidence