Cesium carbonate → HCID 49818751, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[1-(2-chloro-9-ethyl-6-morpholin-4-yl-9H-purin-8-ylmethyl)-piperidin-4-yl]-pyrrolidin-2-one (115 mg, 0.26 mmol), [1-(tert-butyldimethylsilanyl)-5-fluoro-1H-indol-4-yl]boronic acid (105 mg, 0.36 mmol), Pd(PPh3)4 (30 mg, 10 mol %) and cesium carbonate (167 mg, 0.51 mmol) in dioxane/water (5:2 mL) was purged with nitrogen gas then heated at 140° C., for 30 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH then eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si-PPC, MeOH:DCM, gradient 0:100 to 07:93) to give 109 as a colourless oil (13 mg, 9%). LCMS (Method F) RT 8.15 min, [M+H]+ 547.3. 1H NMR (CDCl3, 400 MHz): δ 8.74 (dd, J=9.1, 4.8 Hz, 1H); 8.30 (d, J=3.6 Hz, 1H); 7.28-7.24 (m, 1H); 7.08-6.99 (m, 1H); 6.58 (d, J=3.6 Hz, 1H); 4.42-4.30 (m, 6H); 4.09-3.97 (m, 1H); 3.88 (t, J=4.75 Hz, 4H); 3.72 (s, 2H); 3.35 (t, J=7.0 Hz, 2H); 2.95 (d, J=11.3 Hz, 2H); 2.39 (t, J=8.1 Hz, 2H); 2.32-2.22 (m, 2H); 2.06-1.95 (m, 2H); 1.77-1.61 (m, 4H); 1.52 (t, J=7.15 Hz, 3H)

Provenance & Evidence