反应详情

温度

100 °C

Tricyclic bromide 11 (27 mg, 0.10 mmol) in 1,4-dioxane (1.0 mL) was treated with solid K2CO3 (41 mg, 0.30 mmol), m-nitrophenylboronic acid (34 mg, 0.20 mmol), and water (0.25 mL). The solution was degassed and tetrakis(triphenylphosphine)palladium(0) (12 mg, 10 mol %) was added. The solution was heated at 100° C. for 1 h, then cooled to ambient temperature and diluted with water (2 mL). The aqueous layer was adjusted to pH=7-8 with saturated aqueous K2CO3 and extracted with EtOAc (5 mL×3). The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash chromatography (3-5% MeOH in CHCl3) to yield 14 as a yellow solid, 26.3 mg (87%). mp 268-270° C. (dec.); 1H NMR (DMSO-d6) δ3.16 (m, 2H), 3.45 (m, 2H), 7.33 (m, 1H), 7.65 (m, 1H), 7.76 (m, 1H), 7.78 (m, 1H), 8.30 (m, 1H), 8.53 (bs, 1H), 8.16 (m, 2H), 11.93 (bs, 1H); HRMS (M+Na) Calcd for C17H13N3O3+Na: 330.0855, Found: 330.0847; Anal. (C17H13N3O3.H2O) C, H, N.

1. customThe solution was degassed
2. additiontetrakis(triphenylphosphine)palladium(0) (12 mg, 10 mol %) was added
3. temperaturecooled to ambient temperature
4. additiondiluted with water (2 mL)
5. extractionextracted with EtOAc (5 mL×3)
6. washThe organic solution was washed with water and brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified by flash chromatography (3-5% MeOH in CHCl3)