Tetrabutylammonium Fluoride → 2-[5-(1-hydroxy-ethyl)-1-methyl-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 2-[5-(1-hydroxy-ethyl)-1-methyl-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide (41 mg, 0.08 mmol) was dissolved in tetrabutylammonium fluoride (1.0 M in THF, 0.90 ml, 0.90 mmol). The reaction mixture was stirred at 60° C. overnight then cooled to room temperature, quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then concentrated. The residue was triturated with water, ethyl acetate and a few drops of methanol to afford 21 mg (65%) of 2-[5-(1-hydroxy-ethyl)-1-methyl-1H-indazol-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide as a yellow powder. MS: (M+Na)+=401; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.82 (br. s., 1H), 9.09 (s, 1H), 8.41 (s, 1H), 8.30 (s, 1H), 8.04 (d, J=7.9 Hz, 1H), 7.73 (d, J=8.7 Hz, 1H), 7.55 (d, J=8.3 Hz, 1H), 5.27 (d, J=3.8 Hz, 1H), 4.87-5.00 (m, 1H), 4.19-4.32 (m, 1H), 4.17 (s, 3H), 1.41 (d, J=6.0 Hz, 3H), 1.33 (d, J=6.8 Hz, 6H).

Provenance & Evidence