Benzyl Bromide → HCID 67482428, compound

HRID 2402279Notes

Reaction equation

HRID 2402279 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]([OH:14])=[O:13])[NH:3]1.[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.CCOC(C)=O>[CH2:17]([O:13][C:12](=[O:14])[CH2:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 281699(3-Oxo-2,3-dihydro-1H-isoindol-1-yl)acetic acid

Product 1

HCID 67482428HCID 67482428, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3-Oxo-2,3-dihydro-1H-isoindol-1-yl)-acetic acid (100 mg, 0.52 mmol) was dissolved in 2 mL dry DMF and stirred under N2 at 0° C. NaH (44 mg, 1.1 mmol) was added and stirring continued for 0.5 h. Benzyl bromide (0.13 mL, 1.1 mmol) was added, the mixture was warmed to room temperature and stirred for 3 h. The mixture was diluted with EtOAc. The organic phase was washed with 2×10 mL aq LiCl and 10 mL brine, then dried (MgSO4), filtered and evaporated. The title compound was purified by silica gel chromatography (102 mg, 53%).

Workup

  1. stirringstirring
  2. temperaturethe mixture was warmed to room temperature
  3. stirringstirred for 3 h
  4. washThe organic phase was washed with 2×10 mL aq LiCl and 10 mL brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe title compound was purified by silica gel chromatography (102 mg, 53%)

Sources & evidence

ORD record
ord-b13d4127ff2041178d0f56cc096316ad
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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