tert-Butanol → HCID 67354352, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 ml sealed cap glass pressure vessel, 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1K, 1.7 g, 9.0 mmol), diphenylphosphoryl azide (2.1 ml, 9.8 mmol), and TEA (2.5 ml, 18 mmol) were dissolved in THF (10 ml). To this mixture was added t-BuOH (10 ml) and with the cap sealed, the mixture was heated in an oil bath at 85° C. for 4 hrs. After cooling the mixture was transferred into a round bottom flask using THF, concentrated in vacuo and purified using column chromatography (hexanes-ethyl acetate (0-100%)). Pure product fractions were collected and solvents were evaporated to obtain the product tert-butyl 1,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1L, 1.3 g, 56%) as a fluffy white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.49 (s, 9 H) 2.25 (d, J=1.01 Hz, 3 H) 3.66 (s, 3 H) 7.02 (d, J=1.01 Hz, 1 H) 7.59-7.78 (m, 1 H) 8.43 (d, J=1.01 Hz, 1 H) 9.40 (s, 1 H).

Provenance & Evidence