Trifluoroacetic acid → 1-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperazin-2-one

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Reaction Steps

To a stirred solution of tert-butyl 4-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate (4.952 g, 10.97 mmol) in DCM (20 mL) is added trifluoroacetic acid (4.15 mL, 54.84 mmol) over 2 minutes and the reaction stirred for 90 minutes. The reaction is diluted with MeOH and poured on to a SCX2 ion-exchange column. This is flushed with one column volume of MeOH, and then the product collected in the subsequent one column volume flush of 7 M methanolic ammonia. This solution is then concentrated in vacuo to give a brown oil. This is purified by column chromatography on silica, eluting with 0 to 40% MeOH in EtOAc, to give the title compound as an orange oil (2.989 g, 8.51 mmol). MS (m/z): 352 (M+1).

Provenance & Evidence