反应详情

温度

100 °C

A solution of Example A3 (0.500 g, 1.882 mmol) in dioxane (10 mL) was sparged with Ar, treated with N,N-dimethylurea (0.829 g, 9.41 mmol), XANTPHOS (218 mg, 0.376 mmol), and Cs2CO3 (1.226 g, 3.76 mmol), sparged with Ar, treated with Pd2(dba)3 (0.172 g, 0.188 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT and diluted with EtOAc. The solids were removed via filtration through diatomaceous earth and washed with EtOAc. The filtrates were concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (511 mg, 86%). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.25-8.19 (m, 2H), 7.82 (d, J=8.7 Hz, 1H), 7.50 (d, J=2.3 Hz, 1H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 2.89 (s, 6H), 2.73 (s, 3H); MS (ESI) m/z: 318.1 (M+H+).

1. customsparged with Ar
2. customsparged again with Ar
3. temperatureThe mixture was cooled to RT
4. additiondiluted with EtOAc
5. customThe solids were removed via filtration through diatomaceous earth
6. washwashed with EtOAc
7. concentrationThe filtrates were concentrated to dryness
8. custompurified via silica gel chromatography (MeOH/EtOAc)