Potassium Carbonate → HCID 57812309, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-furo[3,2-c]pyridin-6-ylamine (601 mg, 1.43 mmol), 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (810 mg, 2.1 mmol) and potassium carbonate (590 mg, 4.3 mmol) in 1,4-dioxane (10 mL) and H2O (3 mL) was degassed and refilled with argon (3×) prior to the addition of PdCl2(dppf) (105 mg, 0.143 mmol). The reaction mixture was degassed and refilled with argon (2×) and heated at 100° C. for 2 h (conventional heating). The mixture was diluted with EtOAc (60 mL), then washed with brine (20 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex:EtOAc=50:50→20:80→100% EtOAc) to give the title compound as a light-yellow solid. LC-MS (ES+): 590.07/592.09 [MH+]. 1H NMR (CDCl3, 400 MHz): δ 1.49 (s, 9H), 1.90 (d, J=6.8 Hz, 3H), 1.91-2.02 (m, 2H), 2.17-2.20 (m, 2H), 2.93 (m, 2H), 4.27-4.36 (m, 3H), 5.24 (br s, 2H), 6.62 (q, J=6.8 Hz, 1H), 7.07 (dd, J=8.8, 7.8 Hz, 1H), 7.30 (dd, J=8.8, 4.8 Hz, 1H), 7.55 (s, 1H), 7.68 (s, 1H), 7.75 (s, 1H), 8.11 (s, 1H).

Provenance & Evidence