Diethyl Ether → HCID 11489516, compound

Participants

Reaction Steps

A solution of 4-(3-formyl-1-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (60 mg, 0.15 mmol) in dichloromethane (6 mL) is treated with trifluoroacetic acid (0.18 mL, 0.18 mmol). The resulting solution is allowed to stir at room temperature for 4 days to form a creamy suspension before treating the reaction with a further aliquot of trifluoroacetic acid (0.20 mL, 2.0 mmol) to give an orange solution. After stirring for a further 20 hours, the reaction mixture is evaporated to give an orange oil. Trituration of the crude product salt with acetonitrile and ether gives 54 mg of 2-piperazin-1-yl-1-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde; bis-trifluoro-acetic acid salt as a tan solid (68% yield). LC/MS: retention time 1.72 min, m/e 308 (M+H). 1H NMR (300 MHz, DMSO-d6): 10.16 (1H, s), 8.86 (1H, d), 8.78 (2H, br.s), 8.74 (1H, d), 8.41 (1H, d), 8.17-8.13 (2H, m), 7.70 (1H, dd), 7.30 (1H, dd), 3.50-3.46 (4H, m), 3.06-3.00 (4H, m).

Provenance & Evidence