Sodium hydride → 1-(2,6-difluoro-4-nitrophenyl)-3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

HRID 2206234ノート

反応式

HRID 2206234 の反応式
[I:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[N:8][CH:9]=[CH:10][C:5]=2[NH:4][CH:3]=1.C1OCCOCCOCCOCCOC1.[H-].[Na+].[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([F:40])[C:32]=1F>CN(C=O)C>[F:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([F:40])[C:32]=1[N:4]1[C:5]2[CH:10]=[CH:9][N:8]=[C:7]([O:11][CH3:12])[C:6]=2[C:2]([I:1])=[CH:3]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27827931,2,3-Trifluoro-5-nitrobenzeneHCID 247294143-Iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

生成物 1

HCID 1179883961-(2,6-difluoro-4-nitrophenyl)-3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-iodo-4-methoxy-1H-pyrrolo[3,2-c]pyridine (200 mg) in DMF (6 ml) were added 15-crown-5 (0.159 ml) and sodium hydride (60% dispersion in mineral oil, 32.1 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added 1,2,3-trifluoro-5-nitrobenzene (0.101 ml), and the mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (258 mg).

後処理

  1. stirringthe mixture was stirred overnight at room temperature under nitrogen atmosphere
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-119291fef59c4f8ebb663a72f7e40544
出典データセット
uspto-grants-2016_06
特許番号
US09371320B2

反応ノート

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