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

HRID 427267Notes

Reaction equation

HRID 427267 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-1-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 mL of ice water. The aqueous was extracted with ethyl acetate and the combined organic extracts were washed with 1N HCl, brine, dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated. The crude product was purified by silica gel column chromatography (ethyl acetate/hexane, 3/7) to give 4.1 g (79%) of the title compound as a solid: mp 74° C. (Lit. mp 99° C.; EP 464604 A2).

Workup

  1. extractionThe aqueous was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with 1N HCl, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated
  6. customThe crude product was purified by silica gel column chromatography (ethyl acetate/hexane, 3/7)

Sources & evidence

ORD record
ord-365eb46632ab4f95a5e4638fcf6c797a
Source dataset
uspto-grants-2001_11
Patent number
US06313114B1

Reaction notes

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