2-Chloro-3-pyridinecarboxaldehyde → 2-((4-Fluorophenyl)sulfonyl)nicotinaldehyde

HRID 41868

反応式

HRID 41868 の反応式
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Na+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CS(C)=O.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 7376072-Chloro-3-pyridinecarboxaldehydeHCID 236662204-fluorobenzenesulfinic acid sodium salt

生成物 1

HCID 593805832-((4-Fluorophenyl)sulfonyl)nicotinaldehyde収率 545.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-3-pyridinecarboxaldehyde (4.04 g, 2.86 mmol) and 4-fluorobenzenesulfinic acid sodium salt (5.73 g, 3.14 mmol) were dissolved in DMSO (100 ml) and the mixture was heated at 100° C. for 72 h under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3×). The combined organics were washed with water, brine, dried (MgSO4) and evaporated to dryness to afford 7.89 g of crude product. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluting with heptane using an EtOAc gradient, to afford 4.14 g (41%) of the desired product as a yellow solid (plates) (MP=131-131.3° C.; IR=1691 cm−1; HPLC=7.21 min>99%).

後処理

  1. temperatureUpon cooling to ambient the mixture
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customto afford 7.89 g of crude product
  7. customThe crude compound was pre-absorbed onto silica
  8. custompurified
  9. customby dry pad suction column chromatography
  10. washeluting with heptane using an EtOAc gradient

出典と根拠

ORDレコード
ord-d367e75b4b36450895f3a8ff88c05948
出典データセット
uspto-grants-2013_09
特許番号
US08536158B2

関連ノート

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