Potassium Carbonate → HCID 71093636, compound

Participants

Reaction Conditions

Reaction Steps

4-(3-Fluoroazetidin-1-yl)-1-methyl-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidine (C11) (300 mg, 1.04 mmol), 1-bromo-4-cyclopropylbenzene (617 mg, 3.13 mmol), and potassium carbonate (289 mg, 2.09 mmol) were combined in 1,4-dioxane (7 mL). Palladium(II) acetate (98%, 50.2 mg, 0.219 mmol) was added, and the reaction mixture was heated at 100° C. for 48 hours. Solids were removed via filtration, and the filtrate was concentrated in vacuo. Purification using silica gel chromatography [Gradient: 25% to 50% (10% methanol in ethyl acetate) in heptane] provided the product as a glass. Yield: 205.3 mg, 0.509 mmol, 49%. LCMS m/z 404.2 (M+1). 1H NMR (400 MHz, CD3OD) δ 0.61-0.66 (m, 2H), 0.91-0.97 (m, 2H), 1.81-1.89 (m, 1H), 3.77-3.95 (br m, 2H), 3.91 (s, 3H), 3.95 (s, 3H), 4.07-4.26 (br m, 2H), 5.15-5.36 (m, 1H, JHF=57.5 Hz), 7.05 (br d, J=8.2 Hz, 2H), 7.23 (br d, J=8.4 Hz, 2H), 7.71 (s, 1H), 8.20 (s, 1H).

Provenance & Evidence