Sodium hydride → N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide

HRID 1423011노트

반응식

HRID 1423011 반응식
[Br:1][C:2]1[C:3]([CH2:8]Br)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=[O:16])=[CH:13][CH:12]=1.[H-].[Na+]>C1COCC1.[Cl-].[NH4+]>[Br:1][C:2]1[C:3]([CH2:8][NH:17][C:15](=[O:16])[C:14]2[CH:18]=[CH:19][C:11]([F:10])=[CH:12][CH:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 715724-FluorobenzamideHCID 214410813-Bromo-2-(bromomethyl)pyridine

생성물 1

HCID 67194294N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매

실험 절차

To a mixture of 3-bromo-2-bromomethyl-pyridine (1.30 g, 5.18 mmol) and 4-fluoro-benzamide (725 mg, 5.21 mmol) in THF (20 mL) is added 60% sodium hydride in mineral oil (210 mg, 5.3 mmol) and the mixture is warmed at reflux. After 24 hours, the mixture is diluted with saturated aqueous ammonium chloride (25 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers are washed with brine (2×25 mL), dried over magnesium sulfate, filtered and concentrated. The residue is purified by silica gel chromatography eluting using a gradient of 5-25% EtOAc in hexanes to afford N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide.

후처리

  1. temperaturethe mixture is warmed
  2. temperatureat reflux
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. washThe combined organic layers are washed with brine (2×25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel chromatography
  9. washeluting

출처 및 근거

ORD 기록
ord-8a02188730a2453d9db6f5dc18aef464
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927550B2

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