4-Toluenesulfonyl chloride → HCID 58797893, compound

HRID 1810117Notes

Reaction equation

HRID 1810117 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[I:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[H-].[Na+].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(OCC)(=O)C>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[C:7]2[C:12]([C:13]=1[I:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1487679methyl 3-iodo-1H-indole-2-carboxylate

Product 1

HCID 58797893HCID 58797893, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-iodoindol-2-carboxylic acid methyl ester (202) (0.604 g, 2 mmol) and NaH (60%, 0.192 g, 2.4 mmol) in DMF (20 mL) was added p-toluenesulfonylchloride (0.381 g, 2 mmol) at room temperature. After stirring for 1 hour, ethyl acetate (50 mL) was added to the reaction mixture. The mixture was washed with brine (3×30 mL). The organic layer was dried with MgSO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography (10% ethyl acetate/hexane V:V) to afford 203 (0.68 g, 76%). 1H NMR (CDCl3): 2.35 (s, 3H), 4.05 (s, 3H), 7.23 (d, 2H, J=8.4), 7.33 (t, 1H, J=7.2), 7.41, (m, 2H), 7.83 (d, 2H, J=8.4), 7.98 (d, 1H, J=8.4).

Workup

  1. washThe mixture was washed with brine (3×30 mL)
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by flash chromatography (10% ethyl acetate/hexane V:V)

Sources & evidence

ORD record
ord-a0f541fe1e7b41799873d4483b563772
Source dataset
uspto-grants-2013_01
Patent number
US08362066B2

Reaction notes

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