tert-Butanol → HCID 71087194, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 ml sealed cap glass vessel, 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (1O, 1.75 g, 8.57 mmol), Diphenylphosphoryl azide (2.408 ml, 11.14 mmol), and TEA (2.389 ml, 17.14 mmol) were dissolved in THF (Ratio: 1.000, Volume: 6.00 ml) and added t-BuOH (Ratio: 1.000, Volume: 6 ml) and sealed the cap and heated on oil bath at 85° C. for 2 hrs. Then transferred into round bottom flask using THF, evaporated the reaction mixture and purified using column chromatography (Hexane-Ethyl acetate mixtures). Pure product fractions were collected and concentrated to obtain the product tert-butyl 1-ethyl-3-methyl-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (1P, 0.9 g, 38% yield) as a fluffy white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (t, J=7.20 Hz, 3H) 1.49 (s, 9H) 2.26 (d, J=1.26 Hz, 3H) 4.06 (q, J=7.24 Hz, 2H) 7.10 (d, J=1.01 Hz, 1H) 7.73 (s, 1H) 8.33-8.51 (m, 1H) 9.49 (br. s., 1H).

Provenance & Evidence