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Cesium carbonate → Acetic acid,2-[(7-bromo-2,3-dihydro-3-oxo-1h-isoindol-5-yl)oxy]-,1,1-dimethylethyl ester

HRID 1247453
Notes
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Reaction equation

HRID 1247453 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 219075354-Bromo-6-hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 76848946Acetic acid,2-[(7-bromo-2,3-dihydro-3-oxo-1h-isoindol-5-yl)oxy]-,1,1-dimethylethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 104B (103 mg, 0.45 mmol), Cs2CO3 (164 mg, 0.5 mmol) and t-butyl bromoacetate (0.075 mL, 0.5 mmol) in DMF (2.2 mL) was stirred overnight at room temperature, diluted with water, and filtered. The filter cake was dried to give 154 mg (45%) of the desired product. MS (ESI(+)) m/e 342,344 (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe filter cake was dried

Sources & evidence

ORD record
ord-811b382c140144bcb005f6319f7089d1
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07129260B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes