Diisopropylamine → 4-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylic acid

温度

-78 °C

N,N-Diisopropylamine (8.5 ml) was dissolved in anhydrous THF (150 ml), n-butyl lithium (a 1.65 mol/l solution in hexane, 32 ml) was dropwise added thereto at −78° C. in an argon atmosphere, and the mixture was stirred for 5 minutes. The mixture was stirred at room temperature for 3 minutes and then cooled again to −78° C., 3,5-dichloropicoline (7.2 g) was added thereto, and the mixture was stirred for 30 minutes, which was dropwise added at −78° C. over 1 hour in an argon atmosphere to a solution in anhydrous THF (500 ml) of ethyl 4-formyl-7-methoxybenzofuran-2-carboxylate (10 g) obtained in step 1 of Reference Example 1. The mixture was stirred at −78° C. for 2.5 hours and returned to room temperature, and the reaction was quenched by adding water. The reaction mixture was diluted with ethyl acetate, which was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was suspended in isopropanol and the precipitated crystals were collected by filtration to give the desired compound (14.3 g, 87%) as colorless crystals.

1. stirringThe mixture was stirred at room temperature for 3 minutes
2. temperaturecooled again to −78° C.
3. stirringthe mixture was stirred for 30 minutes
4. stirringThe mixture was stirred at −78° C. for 2.5 hours
5. customreturned to room temperature
6. customthe reaction was quenched
7. additionby adding water
8. additionThe reaction mixture was diluted with ethyl acetate, which
9. washwas washed with a saturated aqueous sodium chloride solution
10. dry with materialdried over sodium sulfate
11. distillationThe solvent was distilled off under reduced pressure
12. filtrationthe precipitated crystals were collected by filtration

ORDレコード

ord-015e93611d4842fda27b071b1c3c073b

出典データセット

uspto-grants-2002_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06395738B1