Dimethylformamide → HCID 57812684, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine (15.0 mg, 0.0357 mmol, 1 eq.), 1-[5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]piperazine (20.6 mg, 0.0714 mmol, 2 eq.), potassium carbonate (14.8 mg, 0.107, 3 eq.) in dioxane (0.9 mL) and water (0.3 mL) was added 1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (1 mg, 0.002 mmol, 0.05 eq.). The mixture was evacuated by vacuum and filled with nitrogen 3 times and heated in a microwave reactor at 100° C. for 30 min. The crude mixture was dried in vacuo, and trimethylsilyl isocyanate (14.5 uL, 0.107 mmol), DIPEA (62.2 uL, 0.357 mmol), and DMF (0.2 mL, 2 mmol) were added. The resulting mixture was stirred at room temperature overnight. The crude solution was passed through Thiol-SPE to remove palladium. The solution was further passed through SCX-2 SPE and the product was released by 2M NH3 in methanol. The solution was concentrated, dissolved in DMSO, and purified on the MDPS. MS (ES+): m/z 545.17/547.17 (100/76) [MH+]. HPLC: tR=0.71 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, DMSO-d6): δ=1.83 (d, J=6.8 Hz, 3H), 3.49-3.57 (m, 8H), 5.63 (s, 2H), 6.07 (s, 2H), 6.27 (q, J=6.7 Hz, 1H), 6.96 (d, J=8.8 Hz, 1H), 7.46 (t, J=8.7 Hz, 1H), 7.53 (dd, J=9.0, 4.9 Hz, 1H), 7.87 (dd, J=8.7, 2.1 Hz, 1H), 8.04 (s, 1H), 8.28 (s, 1H), 8.48 (d, J=2.5 Hz, 1H).

Provenance & Evidence