Sodium hydride → 1H-Pyrrolo(2,3-b)pyridine

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Reaction Steps

To a mixture of 2-propyl-1H-pyrrolo[2,3-b]-pyridine prepared in Example 1 step 3 (0.1M in DMF) is added NaH (1.1 equivalent of an 80% dispersion in oil, 0.271 mmol). After 20 min, 2-t-butoxycarbonyl-4'-bromomethylbiphenyl (1.1 equivalent) is added and the mixture is stirred for 30 min. Water is added and the mixture extracted with EtOAc. Purification by flash chromatography (SiO2, 25% EtOAc/hexanes) gives 2-propyl-1-[(2'-t-butoxycarbonyl)-[1,1']-biphenyl-4-yl)methyl]-1H-pyrrolo[2,3-b]pyridine.

Provenance & Evidence