反应详情

温度

100 °C

Method CC In a 501 mL flask fitted with a reflux condenser, combine 1-isopropyl-6-nitro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (4, R1=i-Pr) (700 mg, 2.1 mmol), 5-(5-Bromo-thiophen-2-yl)-1-methyl-1H-tetrazole (466 mg, 1.9 mmol), tris-(dibenzylideneacetone) di-palladium (0) (17 mg, 0.019 mmol), and tricyclohexylphosphine (13 mg, 0.0047 mmol) in dioxane (5.5 mL). Degas under nitrogen atmosphere three times; then add 1.3M aqueous potassium phosphate (2.5 mL, 3.2 mmol) in a 50 mL flask fitted with a reflux condenser. Heat the reaction mixture to 100° C. for 4 hours. Cool the reaction mixture to room temperature and dilute with water (20 mL) and ethyl acetate (20 mL); then separate layers. Extract the aqueous layer three times with ethyl acetate (10 mL). Combine the organics; dry over MgSO4; remove the solids by filtration; and concentrate the filtrate in vacuo. Purify by silica gel column chromatograph eluting with ethyl acetate in hexanes to afford 0.3 g (39%) of the title material. 1H NMR (CDCl3) δ 8.39 (s, 1H), 8.09 (d, 1H, J=9.1 Hz), 8.02 (d, 1H, J=9.1 Hz), 7.78 (d, 1H, J=3.9 Hz), 7.75 (s, 1H), 7.28 (d, 1H, J=3.9 Hz), 4.79 (quin., 1H, J=6.5 Hz), 4.37 (s, 3H), 1.62 (d, 6H, J=6.5 Hz).

1. customMethod CC In a 501 mL flask fitted with a reflux condenser
2. customDegas under nitrogen atmosphere three times
3. customfitted with a reflux condenser
4. temperatureCool the reaction mixture to room temperature
5. extractionExtract the aqueous layer three times with ethyl acetate (10 mL)
6. dry with materialdry over MgSO4
7. customremove the solids
8. filtrationby filtration
9. concentrationand concentrate the filtrate in vacuo
10. customPurify by silica gel column chromatograph
11. washeluting with ethyl acetate in hexanes