3-Pyridinemethanol → HCID 69894256, compound

Participants

Reaction Steps

Under nitrogen atmosphere, triphenylphosphine bound resin (0.41 g, 0.45 mmol, 1.12 mmol/g) was swelled in dichloromethane for 30 minutes. 3-(5-Methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindol-8-ol (0.1 g, 0.30 mmol) (prepared by Example 3 step (a)), 3-hydroxymethylpyridine (44 μl, 0.45 mmol, 1.5 eq.) and diethyl azodicarboxylate (71 μl, 0.45 mmol, 1.5 eq.) were added and the reaction was stirred at room temperature overnight. The resin was filtered off and washed with dichloromethane, methanol and diethyl ether. The combined organics were concentrated in vacuo. The residue was purified firstly by alumina chromatography, eluting with 1% methanol/dichloromethane, and secondly by silica chromatography, using dichloromethane→5% methanol/dichloromethane as the eluant, to afford the title compound (21 mg, 16%). 1H NMR (400 MHz, CDCl3) δ 8.70–8.69 (1H, m), 8.61–8.59 (1H, m), 7.80 (1H, dt, J=7.8, 2.1 Hz), 7.59 (1H, d, J=2.4 Hz), 7.54–7.52 (2H, m), 7.46–7.33 (4H, m), 7.18 (1H, d, J=8.4 Hz), 7.02 (1H, dd, J=8.4, 2.4 Hz), 5.16 (2H, s), 3.96 (2H, s), 2.70 (3H, s). m/z (ES+) 422 (M+H)+.

Provenance & Evidence