Methyl chloroformate → methyl 4-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 1-[1-ethyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]piperazin-2-one (0.200 g, 0.569 mmol) in DCM (10 mL) is added triethylamine (0.095 mL, 0.683 mmol), followed by methyl chloroformate (0.052 mL, 0.683 mmol). The reaction is then stirred overnight. 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. The solution is then concentrated in vacuo to give the title compound as an orange oil (0.1643 g, 0.401 mmol). MS (m/z): 410 (M+1). 1H-NMR (300.13 MHz, CDCl3): δ 1.37 (t, 3H). 3.79 (s, 3H), 3.74-3.82 (br, 2H), 3.83-3.90 (br, 2H), 4.15 (q, 2H), 4.27-4.39 (br, 2H), 5.58 (s, 2H), 6.71 (d, 1H), 7.04 (s, 1H), 7.19 (t, 1H), 7.45-7.50 (m, 1H), 7.64-7.70 (m, 2H), 8.60 (d, 1H).

Provenance & Evidence