Methanesulfonyl chloride → HCID 86681653, compound

HRID 571236Notes

Reaction equation

HRID 571236 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])[C:6](=[O:16])[CH2:5]2.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:17][S:18]([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])[C:6](=[O:16])[CH2:5]2)(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 43446487HCID 43446487, compound

Product 1

HCID 86681653HCID 86681653, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 2-(5-amino-2-oxoindolin-1-yl)acetate (0.120 g, 0.545 mmol) in pyridine (8 ml) cooled to 0° C., methanesulfonyl chloride (0.047 ml, 0.599 mmol) was added, and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The solvent was removed and the crude was portioned between DCM and 1N HCl. The organic phase was dried over sodium sulfate, and the solvent was removed. The crude was purified by filtration on silica gel cartridge (DCM:MeOH from 99:1 to 97:3) affording methyl 2-(5-(methylsulfonamido)-2-oxoindolin-1-yl)acetate (0.133 g, 0.446 mmol, 82% yield). MS/ESI+ 298.9 [MH]+.

Workup

  1. customThe solvent was removed
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was removed
  4. filtrationThe crude was purified by filtration on silica gel cartridge (DCM:MeOH from 99:1 to 97:3)

Sources & evidence

ORD record
ord-0591cb7773964d26af0c89cb1a8db796
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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