Water → HCID 10292063, compound

Participants

Reaction Steps

2-(4-Fluorophenyl)-3-(4-pyridinyl)pyrazolo[1,5-a]pyridin-5-ol (Example 24. 0.5 g, 1.63 mmol) was dissolved in dimethylformamide (10 mL) and potassium tert butoxide (2.5 mL of a 1 M solution in THF, 2.5 mmol) was added dropwise to the stirred solution. After 10 minutes iodobutane (2 mmol) was added and the reaction stirred at room temperature. Second additions of iodobutane (0.88 mmol) and 1M potassium tertbutoxide (2.5 mL, 1 mmol) were made after 4 h and reaction stirred further until complete by TLC. Water (100 mL) was added and the resulting aqueous solution was extracted with with dichloromethane (4×100 mL), the combined organic solution was dried (MgSO4), filtered and concentrated to give the crude product. This was purified either by silica gel chromatography to give the title compound (58%). 1H NMR (d6-DMSO) δ 0.93 (t, J=7.3 Hz, 3H), 1.43 (quintet, J=7.3 Hz, 2H), 1.74 (quintet, J=7.3 Hz, 2H), 4.13 (t, J=6.9 Hz, 2H), 6.84 (dd, J=2.4, 7.5 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 7.28 (t, J=8.8 Hz, 2H), 7.53 (dd, J=0.5, 8.8 Hz, 2H), 7.73 (d, J=6.4 Hz, 2H), 8.65 (d, J=6.4 Hz, 2H), 8.74 (d, J 7.5 Hz, 1H); APESI-MS m/z 362 (M+1)+.

Provenance & Evidence