Sodium hydride → Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate

HRID 2390240노트

반응식

HRID 2390240 반응식
[CH3:1][C:2]([O:5][C:6]([CH2:8][OH:9])=[O:7])([CH3:4])[CH3:3].[H-].[Na+].[Br:12][C:13]1[C:14](Cl)=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=1>C1COCC1>[C:2]([O:5][C:6](=[O:7])[CH2:8][O:9][C:14]1[C:13]([Br:12])=[CH:18][C:17]([Cl:19])=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:1]

참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 11815394Tert-butyl 2-hydroxyacetate2회HCID 129015963-Bromo-2,5-dichloropyridine

생성물 1

HCID 58521889Tert-butyl[(3-bromo-5-chloropyridin-2-yl)oxy]acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 2-tert-butyl glycolate (437 mg; 3.31 mmol) in anhydrous THF (5 mL) was treated with NaH (159 mg; 3.97 mmol) and stirred at RT for 10 minutes before treating with a solution of 3-bromo-2,5-dichloropyridine (Matrix; 500 mg; 2.20 mmol) in anhydrous THF (5 mL). The resulting reaction mixture was stirred for 22 hours. The reaction mixture was treated with a solution of 2-tert-butyl glycolate (437 mg; 3.31 mmol) in THF (2 ml), then with NaH (159 mg; 3.97 mmol) and the reaction mixture was stirred for 16 h. The reaction was quenched with tBuOH, the solvent removed under reduced pressure affording a brown solid, which was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc, affording the title compound as a yellow sticky solid.

후처리

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 22 hours
  3. customThe reaction was quenched with tBuOH
  4. customthe solvent removed under reduced pressure
  5. customaffording a brown solid, which
  6. customwas purified by flash column chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-6652785368514f6cb8ed87741996c671
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273769B2

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