Methanesulfonyl chloride → Methyl 2-(methylsulfonyl)isoindoline-4-carboxylate

HRID 1055405Notes

Reaction equation

HRID 1055405 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([O:21][CH3:22])=[O:20])[C:13]=2[CH2:12][NH:11]1.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C(Cl)Cl>[CH3:26][S:23]([N:11]1[CH2:12][C:13]2[C:14]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=[CH:17][C:18]=2[CH2:10]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 19828512Methyl isoindoline-4-carboxylate

Product 1

HCID 90037438Methyl 2-(methylsulfonyl)isoindoline-4-carboxylateYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIEA (0.438 g, 3.39 mmol) was added to a solution of methyl isoindoline-4-carboxylate (0.5 g, 2.82 mmol) and mesyl chloride (0.36 g, 3.1 mmol) in DCM (10 mL). After 12 h the mixture was concentrated and the residue purified by silica gel chromatography to afford methyl 2-(methylsulfonyl)isoindoline-4-carboxylate (0.37 g 52%) as an off white solid.

Workup

  1. concentrationAfter 12 h the mixture was concentrated
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-fb5db20e137a4845ad96c1d08562cbf6
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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