Tetrabutylammonium Fluoride → HCID 178449397, compound

Participants

Reaction Steps

In a round-bottomed flask, 2-[7-(tert-butyl-dimethyl-silanyloxymethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (85 mg, 0.14 mmol) was dissolved in THF (0.7 ml) and tetrabutylammonium fluoride (1.0 M in THF, 1.4 ml, 1.4 mmol) was added dropwise. The light brown solution was stirred at room temperature for 10 min then heated at 70° C. for 2.5 h. The reaction mixture was cooled to room temperature, quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on silica gel and chromatographed with MeOH/CH2Cl2/0.5% NH4OH (gradient: 0-10% MeOH). The appropriate fractions were combined and concentrated and the residue was triturated with ethyl acetate containing a few drops of methanol to afford 21 mg (41%) of 2-(7-hydroxymethyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as an off-white powder. MS: (M+Na)'=387; 1H NMR (DMSO-d6, 400 MHz): δ (ppm) 13.49 (s, 1H), 12.77 (s, 1H), 9.15 (s, 1H), 8.39 (d, J=8.1 Hz, 1H), 8.36 (d, J=3.0 Hz, 1H), 8.01 (s, 1H), 7.38-7.46 (m, 1H), 7.16-7.25 (m, 1H), 5.37 (t, J=5.6 Hz, 1H), 4.88 (d, J=5.6 Hz, 2H), 1.53 (s, 9H).

Provenance & Evidence