5-fluoro-3-(piperidin-4-yl)-1H-indole → 5-fluoro-3-[1-(2-(4-pyridinyl)acetyl)-4-piperidinyl]-1H-indole

HRID 440925ノート

反応式

HRID 440925 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[N:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](OOC2C(Cl)=CC(Cl)=C(Cl)C=2)=[O:25])=[CH:19][CH:18]=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([C:24](=[O:25])[CH2:23][C:20]2[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=2)[CH2:13][CH2:12]1

参加物

4

反応物 2

HCID 117699295-fluoro-3-(piperidin-4-yl)-1H-indoleHCID 196965283,4,6-Trichlorophenoxy 2-(4-pyridinyl)acetate

生成物 1

HCID 196965245-fluoro-3-[1-(2-(4-pyridinyl)acetyl)-4-piperidinyl]-1H-indole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1.0 gm (3.73 mMol) 5-fluoro-3-(4-piperidinyl)-1H-indole and 2.4 gm (7.5 mMol) 3,4,6-trichlorophenoxy 2-(4-pyridinyl)acetate in 40 mL dimethylformamide were stirred at ambient temperature for 18 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The phases were separated and the organic extract dried over sodium sulfate then concentrated under reduced pressure. The resultant oil was subjected to silica gel chromatography, eluting with a gradient of ethyl acetate containing 0-5% methanol. Fractions shown to contain the desired amide were combined and concentrated under reduced pressure to give 5-fluoro-3-[1-(2-(4-pyridinyl)acetyl)-4-piperidinyl]-1H-indole as a colorless solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. customThe phases were separated
  4. extractionthe organic extract
  5. dry with materialdried over sodium sulfate
  6. concentrationthen concentrated under reduced pressure
  7. washeluting with a gradient of ethyl acetate containing 0-5% methanol
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f44687d66ac94d4984cc8fa527085883
出典データセット
uspto-grants-1996_05
特許番号
US05521196

反応ノート

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