Methyl iodide → 2-Isopropyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine

温度

-78 °C

2-ethyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (5.15 g, 14.70 mmol) was charged into the reaction mixture with 120 mL of THF. This mixture was cooled to −78° C. Lithium diisopropylamide in THF (9.19 mL, 18.37 mmol) was added dropwise to the cooled reaction mixture over a 10 minute period. The reaction mixture was then stirred for 2 hours at −78° C. Iodomethane (3.13 g, 22.05 mmol) was then dissolved in 10 mL of THF. This solution was then added via syringe to the cold reaction mixture. Stirring was continued as the reaction mixture was allowed to gradually warm to room temperature overnight. The reaction mixture was quenched with aqueous ammonium chloride then was extracted 2×300 mL ethyl acetate. The organics were combined, were washed with aqueous LiCl then were dried over magnesium sulfate. These organics were then filtered and concentrated under vacuum. The crude residue was dissolved in DCM and was loaded onto a silica gel column. The column was eluted with 3-4% ethyl acetate/DCM. Clean product fractions were combined and solvents were evaporated yielding 2-isopropyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (4.1 g, 11.25 mmol, 77% yield).

1. additionThis solution was then added via syringe to the cold reaction mixture
2. stirringStirring
3. temperatureto gradually warm to room temperature overnight
4. customThe reaction mixture was quenched with aqueous ammonium chloride
5. extractionthen was extracted 2×300 mL ethyl acetate
6. washwere washed with aqueous LiCl
7. dry with materialthen were dried over magnesium sulfate
8. filtrationThese organics were then filtered
9. concentrationconcentrated under vacuum
10. dissolutionThe crude residue was dissolved in DCM
11. washThe column was eluted with 3-4% ethyl acetate/DCM
12. customsolvents were evaporated

ORDレコード

ord-f69e03916d014de2aa1ae7b735e5ef74

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08946697B1