Water → 1H-Isoindol-1-one, 4-bromo-2,3-dihydro-7-methoxy-

HRID 1247457Notes

Reaction equation

HRID 1247457 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].[C:13]([O-])([O-])=O.[Cs+].[Cs+].CI.O>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH3:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 21907553HCID 21907553, compound

Product 1

HCID 219075551H-Isoindol-1-one, 4-bromo-2,3-dihydro-7-methoxy-Yield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 106D (103 mg, 0.45 mmol) in DMF (4 mL) was treated with Cs2CO3 (162 mg, 0.5 mmol) and methyl iodide (0.03 mL, 0.48 mmol), stirred at room temperature for 3 hours, then poured into water. The resulting precipitate was filtered to give 76 mg (70%) of the desired product. MS (ESI(+)) m/e 242,244 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-26983ef7633a4dfd8fe5b31dd29a466a
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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