Cesium carbonate → HCID 69671365, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chloro-5-vinylbenzonitrile (67 mg, 0.18 mmol), 6-methylpyrimidin-4-ylamine (24 mg, 0.22 mmol), Pd2(dba)3 (4 mg, 0.005 mmol), Xantphos (10 mg, 0.018 mmol) and cesium carbonate (117 mg, 0.36 mmol) in dioxane (2.0 mL) was de-gassed and purged with nitrogen and the reaction mixture was heated at 80° C. in a sealed vial overnight. The resultant mixture was allowed to cool to room temperature, before being partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (70% ethyl acetate in cyclohexane) to afford the title compound as a brown glass (42 mg, 58% yield). 1H NMR (400 MHz, CDCl3): δ 8.72 (s, 1H), 8.55 (br s, 1H), 8.26 (br s, 1H), 7.98-7.75 (m, 3H), 6.80-6.68 (dd, J=17.6, 6.7 1H), 5.99 (d, J=17.5 Hz, 1H), 5.64 (d, J=10.9 Hz, 1H), 2.55 (s, 3H).

Provenance & Evidence