Ethyl p-methylbenzenesulfonate → HCID 68889377, compound

HRID 1760597Notes

Reaction equation

HRID 1760597 reaction equation
[CH2:1](OS(C1C=CC(C)=CC=1)(=O)=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([C:33]=1[OH:34])=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:35])=[O:24])[CH3:21]>CN(C)C=O>[CH2:20]([O:22][C:23]([C:25]1[NH:26][C:27]2[C:32]([C:33]=1[O:34][CH2:1][CH3:2])=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:35])=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 6638Ethyl p-methylbenzenesulfonateHCID 11430Potassium CarbonateHCID 68888794HCID 68888794, compound

Product 1

HCID 68889377HCID 68889377, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Toluene-4-sulfonic acid ethyl ester (274 mg, 1.37 mmol) and potassium carbonate (378 mg, 2.74 mmol) were added to a solution of 3-hydroxy-7-methyl-1H-indole-2-carboxylic acid ethyl ester (300 mg, 1.37 mmol) in N,N-dimethylformamide (3 mL). The mixture was stirred at 50° C. for 16 h, then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, hexane/ethyl acetate 6:1) afforded the title compound (250 mg, 74%). White solid, ISP-MS: m/e=248.2 ([M+H+]).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-9d7ec5a532764432af927927221b9ab3
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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