Ethylenediamine → HCID 71279840, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-tert-butyl-2-(2-methyl-1H-indol-7-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (60 mg, 126 μmol) in DMF (4 mL) was added ethylenediamine (355 mg, 399 μL, 5.9 mmol) then tetrabutylammonium fluoride (389 μL, 389 μmol). The solution was heated to 60° C. with stirring under a nitrogen atmosphere for 20 h. The reaction mixture was cooled, diluted with ether, washed water and brine, then dried (MgSO4), filtered, and concentrated in vacuo to give an oil which slowly crystallized. The crystals were triturated with water twice then dried under vacuum to give N-tert-butyl-2-(2-Methyl-1H-indol-7-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (29 mg) as a yellow solid. MS (M+H)+=348.1; 1H NMR (CDCl3) δ: 8.87 (s, 1H), 8.35 (d, J=3.0 Hz, 1H), 7.65 (d, J=7.8 Hz, 1H), 7.55-7.61 (m, 1H), 7.20-7.30 (m, 2H), 6.33-6.36 (m, 1H), 2.54 (s, 3H), 1.53 (s, 9H).

Provenance & Evidence