Indole-3-Carboxylic Acid → 1-(4-Methoxy-naphthalene-1-sulfonyl)-1H-indole-3-carboxylic Acid

HRID 1174524Notes

Reaction equation

HRID 1174524 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:23][O:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([S:35](Cl)(=[O:37])=[O:36])=[CH:27][CH:26]=1>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH3:23][O:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([S:35]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]2)(=[O:37])=[O:36])=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 69867Indole-3-Carboxylic AcidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 167755014-Methoxynaphthalene-1-sulfonyl chloride

Product 1

HCID 687737281-(4-Methoxy-naphthalene-1-sulfonyl)-1H-indole-3-carboxylic AcidYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1H-indole-3-carboxylic acid (0.5 g, 3.1 mmol) in tetrahydrofuran (20 cm3 at 0° C. was added sodium bis(trimethylsilyl)amide (6.2 cm3, 6.2 mmol) dropwise under nitrogen. The solution was stirred at 0° C. for 30 m before addition of 4-methoxy-1-naphthyl sulfonyl chloride (0.8 g, 3.1 mmol) and the resultant solution was stirred at room temperature for 18 h. The solution was diluted with saturated aqueous sodium bicarbonate solution and washed with ethyl acetate. The aqueous layer was acidified to pH 1 with 5N hydrochloric acid and the product extracted into ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to give the title compound (A) (1.1 g, 93%).

Workup

  1. washwashed with ethyl acetate
  2. extractionthe product extracted into ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-066b6245a3d74dca97de4559de3edf5b
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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