Cesium carbonate → HCID 178489073, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (±)-tert-butyl 4-((5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate and (±)-tert-butyl 4-((6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (0.3 g, 0.533 mmol) was dissolved in THF (5.33 mL). TBAF (5.34 mL, 5.34 mmol) was added to the solution and the reaction was stirred at 50° C. for 5 hours. The reaction was diluted with ethyl acetate and then with 20 mL of a saturated aq. solution of ammonium chloride. The ethyl acetate layer was separated, washed with water, dried and concentrated. The resulting residue was dissolved in MeOH (4 mL) to which cesium carbonate (0.87 g, 2.67 mmol) was added. The reaction was heated at 50° C. for 1 hour. The reaction was then concentrated and directly purified by flash chromatography (0-10% MeOH in DCM) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.93 (d, J=3.54 Hz, 1H) 10.86 (br. s., 1H) 7.81-7.95 (m, 1H) 7.60 (m) 7.40-7.56 (m) 7.14 (t, J=2.78 Hz, 1H) 6.75 (s, 1H) 6.53-6.62 (m, 1H) 6.19-6.31 (m, 2H) 3.81 (s, 3H) 2.40-2.47 (m, 3H). HRMS calcd. for C19H16N4O2 (M+H)+ 333.1346. found 333.1355.

Provenance & Evidence