Sodium hydride → tert-butyl 2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetate

HRID 571268Notes

Reaction equation

[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]2=[O:16])(=[O:5])=[O:4].[H-].[Na+].Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CN(C=O)C>[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:10](=[O:15])[C:9]2=[O:16])(=[O:5])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N,N-dimethyl-2,3-dioxoindoline-5-sulfonamide (0.639 g, 2.51 mmol) in dry DMF (10 ml), cooled at 0° C. under nitrogen, NaH (60% dispersion in mineral oil, 0.111 g, 2.76 mmol) was added. The mixture turned dark blue. After stirring at 0° C. for 30 minutes, tert-butyl bromoacetate (0.446 ml, 3.02 mmol) was added, and the mixture was stirred at room temperature for 36 hours. The mixture was partitioned between ethyl acetate and brine and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness affording tert-butyl 2-(5-(N,N-dimethylsulfamoyl)-2,3-dioxoindolin-1-yl)acetate (0.926 g, 2.51 mmol). MS/ESI+ 368.9 [MH]+.

Workup

stirringthe mixture was stirred at room temperature for 36 hours
customThe mixture was partitioned between ethyl acetate and brine
extractionthe aqueous phase was extracted three times with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-01f6253bcf054ef8b57410011a6c99d3
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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