Hexachloroethane → 3-(2-Butynyl)-2,4-dichloro-3H-imidazo[4,5-c]pyridine

2.22 ml of a tetrahydrofuran solution of lithium diisopropylamide was added dropwise to a 5 ml tetrahydrofuran solution of 490 mg of 3-(2-butynyl)-4-chloro-3H-imidazo[4,5-c]pyridine in a dry ice-methanol bath, and the mixture was stirred below −66° C. for 20 minutes. The resulting reaction mixture was added dropwise to a 2 ml tetrahydrofuran solution of 1.13 g of hexachloroethane while the temperature of the mixture was controlled to be −63° C. or lower. The mixture was stirred for one hour and 40 minutes in the same bath, and then a saturated aqueous ammonium chloride solution was added thereto. The resulting mixture was extracted twice with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate, then filtered. The filtrate was concentrated under reduced pressure. Then, the resulting residue was purified by silica gel column chromatography. Thus, 120 mg of brown oily material was obtained from the fraction eluted with hexane-ethyl acetate (2:1).

1. customThe resulting reaction mixture
2. customto be −63° C.
3. stirringThe mixture was stirred for one hour and 40 minutes in the same bath
4. extractionThe resulting mixture was extracted twice with ethyl acetate
5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customThen, the resulting residue was purified by silica gel column chromatography

ORDレコード

ord-8adadceae381408d99ea7a971222e9dd

出典データセット

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07772226B2