Methanesulfonyl chloride → HCID 86681621, compound

HRID 571209Notes

Reaction equation

HRID 571209 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 431653941094646-15-7

Product 1

HCID 86681621HCID 86681621, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-(5-amino-1H-indol-1-yl)acetate (730 mg, 3.54 mmol) in pyridine (15 ml), methanesulfonyl chloride (418 μl, 5.36 mmol) was added, and the mixture was reacted for 2 hours at room temperature. The solvent was evaporated and the resulting crude was partitioned between 1N HCl and ethyl acetate; the aqueous phase was extracted with ethyl acetate (3×30 ml) and dried over sodium sulfate. The solvent was removed obtaining crude methyl 2-(5-(methylsulfonamido)-1H-indol-1-yl)acetate that was used in the next step without any additional purification (1 g, 3.54 mmol, quantitative yield). MS/ESI+ 283.3 [MH]+.

Workup

  1. customthe mixture was reacted for 2 hours at room temperature
  2. customThe solvent was evaporated
  3. customthe resulting crude was partitioned between 1N HCl and ethyl acetate
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×30 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-1fa3df13da0c4a9d9a6176260c0ccabf
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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