Acetic Acid → Methyl 1-[[2-(trimethylsilyl)ethyl]sulfonyl]-1H-indole-5-carboxylate

HRID 1760795Notes

Reaction equation

HRID 1760795 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)=[O:4].[H-].[Na+].[CH3:16][Si:17]([CH3:25])([CH3:24])[CH2:18][CH2:19][S:20](Cl)(=[O:22])=[O:21].C(O)(=O)C>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:20]([CH2:19][CH2:18][Si:17]([CH3:25])([CH3:24])[CH3:16])(=[O:22])=[O:21])[CH:9]=[CH:8]2)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2737635methyl 1H-indole-5-carboxylateHCID 98370862-(Trimethylsilyl)ethane-1-sulfonyl chloride

Product 1

HCID 54384862Methyl 1-[[2-(trimethylsilyl)ethyl]sulfonyl]-1H-indole-5-carboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-indole-5-carboxylic acid methyl ester (3.6 g, 20.6 mmol) in tetrahydrofuran (180 mL) at 0° C., was added sodium hydride (0.65 g, 21.9 mmol). After 10 min., 2-trimethylsilanylethanesulfonyl chloride (4.4 g, 21.9 mmol) was added and the reaction mixture was allowed to warm to room temperature. After 3 h, acetic acid (1.6 mL, 26.8 mmol) was added and the reaction mixture was concentrated. The crude product was chromatographed (Biotage 40M column, 2.5% ethyl acetate-hexanes) to afford 1-(2-trimethylsilanylethanesulfonyl)-indole-5-carboxylic acid methyl ester (5.43 g) as a white solid.

Workup

  1. waitAfter 3 h
  2. concentrationthe reaction mixture was concentrated
  3. customThe crude product was chromatographed (Biotage 40M column, 2.5% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-a16206c36f074f0885cadecc2797465f
Source dataset
uspto-grants-2005_01
Patent number
US06844366B2

Reaction notes

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