2-Mesitylenesulfonyl chloride → HCID 22731441, compound

HRID 1356722Notes

Reaction equation

HRID 1356722 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH3:15])([O:3][CH2:4][CH3:5])=[O:2].[H-].[Na+].[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[S:27](Cl)(=[O:29])=[O:28].[NH4+].[Cl-]>CN(C=O)C>[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:27]([C:20]1[C:21]([CH3:26])=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=1[CH3:18])(=[O:29])=[O:28])[CH:10]=[C:9]2[CH3:15])([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 130462-Mesitylenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12628587Ethyl 3-methyl-1H-indole-5-carboxylate

Product 1

HCID 22731441HCID 22731441, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-carboethoxy-3-methylindole (601 mg, 2.96 mmol) in DMF, sodium hydride (178 mg, 4.45 mmol) and 2,4,6-trimethylbenzenesulfonyl chloride (971 mg, 4.44 mmol) were added under cooling with ice, followed by stirring for 30 min. The reaction mixture was mixed with a saturated aqueous NH4Cl solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5) to give the titled compound (1.02 g, 90%). NMR (method a, CDCl3): δ 1.40 (3H, t, J=7.0 Hz), 2.29 (3H, s), 2.32 (3H, s), 2.52 (6H, s), 4.38 (2H, q, J=6.9 Hz), 6.95 (2H, s), 7.35 (1H, s), 7.41 (1H, d, J=8.9 Hz), 7.90 (1H, dd, J=1.4, 8.9 Hz), 8.24 (1H, s).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-05fa2f41682d47d080d7312dde8f61bf
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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