Tetrabutylammonium Fluoride → HCID 178508367, compound

Participants

Reaction Steps

4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amine (25 mg, 0.046 mmol) was dissolved in THF (1.00 mL) and tetra-n-butylammonium fluoride (1.0 M in THF, 1.00 mL, 1.00 mmol) was added and stirred at RT for 16 h. The reaction was then washed with sodium bicarbonate and water (2×). The organic layer was collected, dried over sodium sulfate, filtered, and then concentrated in vacuo to a solid. Purification by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc) afforded 5.5 mg (28%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 9.33 (d, J=0.51 Hz, 1H), 8.57 (d, J=6.06 Hz, 1H), 8.49 (d, J=6.06 Hz, 1H), 8.35 (dd, J=7.33, 1.26 Hz, 1H), 8.24 (d, J=8.08 Hz, 1H), 8.11 (s, 1H), 7.92 (s, 1H), 7.90 (d, J=0.76 Hz, 1H), 7.83 (dd, J=8.21, 7.45 Hz, 1H), 7.50 (s, 1 H), 4.25 (tt, J=11.84, 3.82 Hz, 1H), 3.69 (tt, J=10.89, 4.26 Hz, 1H), 2.07-2.22 (m, 4H), 1.95-2.05 (m, 2H), 1.45-1.57 (m, 2H); MS (ESI): 427.19 [M+H]+; HPLC tR=0.87 min (TOF: polar—3 min).

Provenance & Evidence