Cesium carbonate → 2-Chloro-3-cyclopropylpyrazolo[1,5-A]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of the title compound from Example 1 Step A (0.250 g, 0.898 mmol), palladium acetate (0.020 g, 0.090 mmol), cyclopropyl boronic acid (0.154 g, 1.80 mmol), cesium carbonate (0.878 g, 2.69 mol), and triphenylphosphine (0.047 g, 0.180 mmol) in tetrahydrofuran (8.98 mL) was heated in a sealed tube at 100° C. for 18 hours. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. Purification of the resulting residue by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound: LCMS m/z 192.93 [M+H]+, 194.89 [M+2+H]+; 1H NMR (500 MHz, CDCl3) δ 8.29 (d, J=7.0 Hz, 1 H), 7.49 (d, J=12.8 Hz, 1 H), 7.21 (dd, J=7.5, 7.5 Hz, 1 H), 6.70 (dd, J=6.3, 6.3 Hz, 1 H), 1.79-1.74 (m, 1 H), 0.98-0.95 (m, 2 H), 0.75-0.73 (m, 2 H).

Provenance & Evidence