Morpholine → HCID 46913522, compound

Participants

Reaction Conditions

Reaction Steps

To a 5 mL microwave tube was added 6-bromo-3-(5,6-dimethoxypyridin-3-yl)imidazo[1,2-a]pyridine (0.050 g, 0.15 mmol), morpholine (0.020 g, 0.22 mmol), 2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene (0.0028 g, 0.0045 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.0014 g, 0.0015 mmol), sodium tert-butoxide (0.020 g, 0.21 mmol), and toluene (3 mL). The resulting reaction mixture was sealed and heated to 100° C. in closed system for 6 h. The reaction was cooled and the solvent was removed. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, 12 g SiO2, DCM:MeOH=96%:4%, Flow=30 mL/min). The product fractions were collected. The solvent was removed in vacuo to afford the desired product as white solid (10.0 mg). MS (ESI pos. ion) m/z: 341.0. Calcd exact mass for C18H20N4O3: 340.2. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.99-3.09 (m, 4H) 3.84-3.92 (m, 4H) 3.94 (s, 3H) 4.11 (s, 3H) 7.12 (d, J=9.79 Hz, 1H) 7.17 (s, 1H) 7.57-7.65 (m, 3H) 7.96 (s, 1H).

Provenance & Evidence