Tetrabutylammonium Fluoride → HCID 71280658, compound

Participants

Reaction Steps

To a solution of N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine-3-carboxamide (64) (230 mg, 0.39 mmol) in THF (5 mL), was added TBAF (1M in THF, 0.43 mL) and the resulting mixture was stirred for 1 hour. THF was removed and the residue was added to a mixture of water (10 mL), MeOH (5 mL) and EtOAc (5 mL). Organic solvents were removed slowly to give a precipitate which was filtered and dried to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(hydroxymethyl)imidazo[1,2-a]pyridine-3-carboxamide (F37). 1H NMR (400 MHz, CDCl3) δ 9.39 (m, 1H), 8.42 (d, J=1.6 Hz, 1H), 8.04 (s, 1H), 7.70 (dd, J=1.7, 7.9 Hz, 1H), 7.60 (d, J=9.2 Hz, 1H), 7.42 (s, 1H), 7.36 (dd, J=1.7, 9.2 Hz, 1H), 7.23 (d, J=8.1 Hz, 1H), 4.63 (d, J=5.7 Hz, 2H), 3.63-3.41 (m, 1H), 3.09-2.85 (m, 4H), 2.28 (s, 3H), 1.82 (t, J=5.9 Hz, 1H). MS m/z 440.1 (M+1)+.

Provenance & Evidence