Ethanol → HCID 58382138, compound

Participants

Reaction Steps

To the suspension of ethyl 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.77 g, 1.9 mmol) in 1,4-dioxane (12 mL) was added aquoeous NaOH (1 N, 12 mL, 12 mmol). The mixture was stirred at rt for about 48 h. To the mixture was added EtOH (1 mL) and the mixture was heated at about 50° C. for about 24 h. The mixture was concentrated under reduced pressure and aqueous HCl (0.5 M, 10 mL) was added and the mixture extracted with EtOAc (25 mL). The solid in the organic layer was collected by vacuum filtration. The filtrate and aqueous layer were recombined and separated. The solid was dissolved in EtOAc (˜150 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo and dried under reduced pressure at about rt to give 4-(cyclohexylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.713 g, 99%): LC/MS (Table 2, Method b) Rt=2.74 min.; MS m/z: 390 (M+H)+.

Provenance & Evidence