Potassium Carbonate → HCID 67520829, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-benzofuran-2-yl-5-bromopyridin-2-ylamine (65.2 mg, 0.226 mmol, 1 eq), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (56.7 mg, 0.272 mmol, 1.2 eq), Pd(PPh3)4 (18.6 mg, 0.0161 mmol, 7 mol %), and potassium carbonate (101.1 mg, 0.732 mmol, 3.2 eq) in a 4:1 mixture of DME:H2O (2.5 mL) was evacuated and charged with nitrogen several times, after which the sample was heated in the microwave reactor to 100° C. for 45 min. EtOAc was added to dilute the reaction, which was then washed with water (2×) and brine (1×), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to dryness. The crude material was purified by column chromatography on silica gel [0.5″×10″ glass column, eluting with CH2Cl2:EtOAc 1:0→4:1→1:1→2:3→3:7→1:9→0:1]. Fractions containing product were combined and concentrated in vacuo. DCM and heptane were added to the residue and the solvent was concentrated in vacuo until all CH2Cl2 had been removed; a solid precipitated at this point. The solid was triturated in hot heptane and filtered off, giving the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=3.86 (s, 3H), 6.28 (br s, 2H), 7.24-7.37 (m, 2H), 7.39 (d, J=0.8 Hz, 1H), 7.64-7.70 (m, 2H), 7.86 (d, J=0.8 Hz, 1H), 8.11 (d, J=2.3 Hz, 1H), 8.13 (s, 1H), 8.31 (d, J=2.3 Hz, 1H). MS (ES+): m/z=291.09 (100) [MH+]. HPLC: tR=2.65 min (ZQ3, polar—5 min).

Provenance & Evidence