2-Amino-3-Hydroxypyridine → HCID 67244132, compound

Participants

Reaction Steps

1-(4-fluorophenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonyl chloride (25 mg, 70 μmol) was dissolved in THF (0.5 mL) and placed in a 2 mL microwave vial. To this solution was added 2-aminopyridin-3-ol (8.5 mg, 77 μmol), DIPEA (26 μL, 150 μmol) and a magnetic stirrer bar and the reaction was capped. After stirring at room temperature for 1 hour, conversion to the amide was complete as shown by LCMS. To the crude reaction mixture was added Burgess reagent (83 mg, 350 μmol) and the reaction was heated for 5 minutes at 150° C. on a Biotage Initiator. The reaction mixture was diluted with DCM (3 mL) and saturated aqueous sodium bicarbonate (3 mL). The organic layer was removed and the aqueous layer extracted with DCM (2 mL). The organic layers were combined, dried with sodium sulfate, filtered and evaporated to produce a brown oil that was purified by flash column chromatography on an ISCO HPLC using a 4 gram SiO2 cartridge and a gradient of 25-100% hexanes in EtOAc. This yielded 15 mg (52%) of a yellow oil. LCMS (+ESI) m/z=413.0 [M+H]+; 1H-NMR (CDCl3) δ 9.05 (dd, 2H), 8.60 (d, 1H), 7.95 (dd, 1H), 7.82 (d, 1H), 7.78 (d, 1H), 7.35 (dd, 1H), 7.20 (dd, 2H), 4.12 (t, 2H), 3.96 (t, 2H).

Provenance & Evidence