Lithium Hydroxide → HCID 68887882, compound

Participants

Reaction Conditions

Reaction Steps

Lithium hydroxide (3.3 mg, 0.0795 mmol) was added to a solution of methyl 5-(5-(5-chloro-6-isopropoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl)-4-methylindane-2-carboxylate (17.0 mg, 0.0397 mmol, from Step G) in THF (1.0 mL) and H2O (300 μL) and heated to 50° C. After 30 min, the reaction mixture was concentrated in vacuo and partitioned between EtOAc (5 mL) and 5% citric acid (2 mL). The layers were separated and organic layer was washed with H2O (3×2 mL), brine (1×2 mL) and dried over MgSO4. The mixture was filtered and the filtrated concentrated in vacuo. Purification of the residue by flash chromatography (3% CH3OH/CH2Cl2/1% HCO2H) on SiO2 afforded 15.2 mg of the title compound as a white solid: 1H NMR (500 MHz, CD3OD) δ 1.41 (d, 6H, J=6.2 Hz), 2.51 (s, 3H), 3.19-3.41 (m, 5H), 5.49 (septet, 1H, J=6.2 Hz), 7.17 (d, 1H, J=8.0 Hz), 7.78 (d, 1H, J=7.8 Hz), 8.39 (s, 1H), 8.83 (s, 1H); HPLC A: rt=4.11 min, m/z=414.3 (M+H)+.

Provenance & Evidence