Cesium carbonate → HCID 86726462, compound

Participants

Reaction Conditions

Reaction Steps

The solution of 6-(2-chloro-4-((tetrahydro-2H-pyran-4-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv), 5-amino-6-methoxy-N-methylpicolinamide (1.05 equiv), xantphos (0.2 equiv), tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv) in 1,4-dioxane (0.16 M) was added cesium carbonate (1.4 equiv). The reaction mixture was stirred at 150° C. for 2 h under microwave irradiation. The reaction was filtered, and concentrated. The crude was purified using silica gel chromatography (0-90% ethyl acetate (with 10% 1N ammonia in methanol) in hexane) to give the title compound (82% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.11 (s, 9 H) 0.84-0.93 (m, 2 H) 1.63-1.76 (m, 2 H) 2.03-2.16 (m, 2 H) 2.64 (s, 3 H) 2.84 (d, J=4.69 Hz, 3 H) 3.49-3.65 (m, 4 H) 3.70-3.80 (m, 2 H) 4.12 (s, 3 H) 5.52-5.55 (m, 1 H) 5.58 (s, 2 H) 7.60 (s, 1 H) 7.65 (d, J=1.17 Hz, 2 H) 7.70 (d, J=8.20 Hz, 1 H) 7.91-7.99 (m, 1 H) 8.03 (s, 1 H) 8.41 (q, J=4.69 Hz, 1 H) 8.91 (d, J=7.81 Hz, 1 H); MS (ESI) m/z 660.5 [M+1]+.

Provenance & Evidence