5-Bromoimidazo(1,2-a)pyridine → HCID 49833295, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of dimethyl-[1-(4-morpholin-4-yl-2-(tributylstannanyl)thieno[3,2-d]pyrimidin-6-ylmethyl)piperidin-4-yl]amine (156 mg, 0.24 mmol), 5-bromoimidazo[1,2-a]pyridine (56 mg, 0.29 mmol), Pd(PPh3)4 (28 mg, 0.02 mmol) and copper(I) iodide (55 mg, 0.29 mmol) in THF (2 5 mL) was purged with argon gas then heated at 140° C., for 20 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge (5 g), washed with MeOH then eluted with 2 M NH3 in MeOH. The resulting residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 10:90) to give 688 as a white solid (72 mg, 63%). LCMS (Method F): RT 3.89 min; [M+H]+ 478. 1H NMR (400 MHz, CHCl3-d): δ 9.23 (s, 1 H); 7.95 (dd, J=8.6, 1.3 Hz, 1 H); 7.77 (d, J=8.6 Hz, 1 H); 7.75 (d, J=1.3 Hz, 1 H); 7.35 (s, 1 H); 7.32-7.29 (m, 1 H); 4.07 (t, J=4.8 Hz, 4 H); 3.91 (t, J=4.8 Hz, 4 H); 3.84 (s, 2 H); 3.04 (d, J=11.25 Hz, 2 H); 2.33-2.25 (m, 6 H); 2.21-2.10 (m, 3 H); 1.84 (d, J=12.5 Hz, 2 H); 1.61 (m, 2 H)

Provenance & Evidence