Diisopropylethylamine → 1-(4-methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic Acid

HRID 1174517Notes

Reaction equation

HRID 1174517 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([C:10]([OH:12])=[O:11])[CH2:2]1.C(N(CC)C(C)C)(C)C.[CH3:22][O:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([S:34](Cl)(=[O:36])=[O:35])=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:22][O:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([S:34]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]([C:10]([OH:12])=[O:11])[CH2:2]2)(=[O:36])=[O:35])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 167755014-Methoxynaphthalene-1-sulfonyl chlorideHCID 19697631Indoline-3-carboxylic acid

Product 1

HCID 687698721-(4-methoxynaphthalene-1-sulfonyl)-2,3-dihydro-1H-indole-3-carboxylic AcidYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,3-dihydro-1H-indole-3-carboxylic acid (A) (3.59 g, 22.0 mmol) was added aqueous N,N-dimethylformamide (DMF) (3:2 v/v; 75 cm3), and then N,N-diisopropylethylamine (9.0 cm3, 50.7 mmol). The mixture was stirred at room temperature for 5 min, before 4-methoxy-1-naphthyl sulfonyl chloride (B)(5.64 g, 22.0 mmol) was added. After stirring for a further 16 h at room temperature saturated aqueous sodium bicarbonate (60 cm3) was added and the organic material was extracted into ethyl acetate (60 cm3). The organic layer was then washed with a further portion of saturated aqueous sodium bicarbonate (40 cm3) before the aqueous fractions were combined and acidified to pH 5 with 5N hydrochloric acid. The desired material was then extracted from the acidified aqueous mixture into ethyl acetate (2×60 cm3), which was subsequently dried over sodium sulfate and evaporated under reduced pressure to afford the title compound (C) (6.1 g, 16.1 mmol, 73%).

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe organic material was extracted into ethyl acetate (60 cm3)
  4. washThe organic layer was then washed with a further portion of saturated aqueous sodium bicarbonate (40 cm3) before the aqueous fractions
  5. extractionThe desired material was then extracted from the acidified aqueous mixture into ethyl acetate (2×60 cm3), which
  6. dry with materialwas subsequently dried over sodium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-600cbfdd50754aab9126f9135bc7549e
Source dataset
uspto-grants-2010_11
Patent number
US07838518B2

Reaction notes

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