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

HRID 1937421

반응식

HRID 1937421 반응식
[CH:1](NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[C:15](C)=[N:16][CH:17]=[C:18]([Cl:20])[CH:19]=1.[CH:22]([C:24]1[C:29]2[CH:30]=[C:31]([C:33]([O:35]CC)=[O:34])[O:32][C:28]=2[C:27]([O:38][CH3:39])=[CH:26][CH:25]=1)=[O:23]>C1COCC1.CCCCCC>[Cl:20][C:18]1[CH:17]=[N:16][CH:15]=[C:14]([Cl:13])[C:19]=1[CH2:1][C:22]([C:24]1[C:29]2[CH:30]=[C:31]([C:33]([OH:35])=[O:34])[O:32][C:28]=2[C:27]([O:38][CH3:39])=[CH:26][CH:25]=1)=[O:23]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 22734010Ethyl 4-formyl-7-methoxybenzofuran-2-carboxylateHCID 227343433,5-Dichloro-2-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 227341684-[2-(3,5-Dichloro-4-pyridyl)-1-oxoethyl]-7-methoxybenzofuran-2-carboxylic acid수율 87%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-015e93611d4842fda27b071b1c3c073b
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395738B1

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