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

HRID 1423011ノート

反応式

HRID 1423011 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a02188730a2453d9db6f5dc18aef464
出典データセット
uspto-grants-2015_01
特許番号
US08927550B2

反応ノート

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