Cesium carbonate → HCID 67419373, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product (83 mg, 0.15 mmol) from step B and 6-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (29.3 mg, 0.17 mmol) in DMF (5.0 mL) was added cesium carbonate (0.11 g, 0.35 mmol) and then heated at 60° C. overnight. The reaction solution was cooled to room temperature, diluted with methanol (10 mL) and added potassium carbonate (43.2 mg, 0.31 mmol) to it. The resultant mixture was stirred at room temperature until complete loss of starting material. The reaction solution was then diluted with 9:1 mixture of dichloromethane/methanol, filtered through a syringe filter and concentrated in vacuo. The residue obtained was purified by preparative thin layer chromatography (dichloromethane/methanol 9:1) to give 6-chloro-2-(4-methoxy-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (26.7 mg, 39%): 1H NMR (CD3OD, 500 MHz) δ 7.94 (t, J=1.5 Hz, 1H), 7.48 (d, J=2.5 Hz, 1H), 7.30 (dd, J=8.5, 2.0 Hz, 1H), 7.20-7.17 (m, 2H), 6.95 (d, J=8.5 Hz, 1H), 5.09 (s, 2H), 4.68 (d, J=9.5 Hz, 1H), 3.84 (dd, J=12.0, 2.5 Hz, 1H), 3.80 (s, 3H), 3.65 (dd, J=12.0, 7.0 Hz, 1H), 3.53-3.45 (m, 2H), 3.42-3.35 (m, 2H); ESI MS m/z 452 [M+H]+.

Provenance & Evidence