4-Toluenesulfonyl chloride → 5-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indole

HRID 1596781Notes

Reaction equation

HRID 1596781 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][OH:14].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 150205413-(5-fluoro-1H-indol-3-yl)propan-1-ol

Product 1

HCID 150205425-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indoleYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-(5-fluoro-1H-indol-3-yl)-propan-l-ol (2.90 g, 15.0 mmol) in pyridine (15.0 mL) was added p-toluenesulfonyl chloride (7.1 g, 37.5 mmol) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was poured to 200 nm of ice water. The aqueous was extracted with ethyl acetate and the combined organic extracts were washed with IN HCI and brine. The resulting material was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated under vacuum. The crude product was purified by silica gel column chromatography (ethyl acetatehexane, 3n) to give 4.1 g (79%) of the title compound as a solid: mp 74 CC (Lit. mp 99 ° C.; EP 464604 A2).

Workup

  1. extractionThe aqueous was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with IN HCI and brine
  3. dry with materialThe resulting material was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated under vacuum
  6. customThe crude product was purified by silica gel column chromatography (ethyl acetatehexane, 3n)

Sources & evidence

ORD record
ord-ac37f212a5d84d8ebf7481c256366770
Source dataset
uspto-grants-2001_09
Patent number
US06291683B1

Reaction notes

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