4-Bromoquinoline → HCID 59605440, compound

Participants

Reaction Steps

To a degassed mixture of 2-methyl-2-(4-((4-morpholino-2-(tributylstannyl)thieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propanamide (235 mg, 0.339 mmol), 4-bromoquinoline (60 mg, 0.288 mmol), copper(I) thiophene-2-carboxylate (55 mg, 0.228 mmol) in dioxane (2 mL) was added Pd(PPh3)4 (17 mg, 0.014 mmol). The reaction mixture was reacted in the CEM microwave at 140° C. for 30 min. The reaction mixture was then loaded onto a Biotage Isolute SPE SCX-2 column. The column was washed with MeOH, eluted with 2 M NH3 in MeOH and further purified by RP-HPLC to give 171 (44 mg, 29%). LCMS: M+H+=532.2. 1H-NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 9.04 (s, 1H), 8.86 (d, 1H), 8.22 (d, 1H), 7.84 (t, 1H), 7.73 (t, 1H), 7.47 (s, 1H), 7.06 (s, 1H), 6.94 (s, 1H), 3.97 (m, 4H), 3.88 (s, 2H), 3.68 (m, 4H), 2.54-2.67 (m, 8H), 1.09 (s, 6H)

Provenance & Evidence