Cesium carbonate → 1,1-Dimethylethyl 2-[(7-bromo-2,3-dihydro-3-oxo-1H-isoindol-5-yl)oxy]acetate

HRID 1247453Notes

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]

Participants

6

Reactant 3

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

Product 1

HCID 768489461,1-Dimethylethyl 2-[(7-bromo-2,3-dihydro-3-oxo-1H-isoindol-5-yl)oxy]acetateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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
Patent number
US07129260B2

Reaction notes

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