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

HRID 863469노트

반응식

HRID 863469 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-565c4e4e450c48a498a458375a91fca6
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721252

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