3-Hydroxypyridine → HCID 69201717, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 131A (60.0 mg, 0.143 mmol), di-t-butyl azodicarboxylate (39.6 mg, 0.172 mmol), Ph3P on solid support (3 mmol/g, 57.3 mg, 0.172 mmol), and 3-hydroxypyridine (16.4 mg, 0.172 mmol) in THF (2 mL) was stirred at room temperature overnight. The solid was filtered and the solvent was evaporated. The crude product was treated with HCl (concentrated, 4 drops) and EtOH (4 mL). The mixture was heated in a capped vial at 75° C. for 2 hours. The solvent was evaporated and the residue was purified using reversed-phase HPLC to give the desired product (12.4 mg) as TFA salt. MS (ESI) m/z: 366.0 (M+H)+. 1H NMR (300 MHz, DMSO-D6) δ ppm 4.01 (s, 2H) 5.83 (s, 2H) 7.58 (d, J=7.80 Hz, 1H) 7.74 (m, 1H) 7.80 (s, 1H) 7.93-8.05 (m, 2H) 8.18 (d, J=8.14 Hz, 1H) 8.40 (dd, J=8.14, 2.37 Hz, 1H) 8.62-8.84 (m, 2H) 9.19 (s, 1H) 12.14 (s, 1H).

Provenance & Evidence