2-Fluoroethyl bromide → 7-Dibenzylamino-2-(2-fluoro-ethyl)-3,3-dimethyl-2,3-dihydro-isoindol-1-one

HRID 2112109Notes

Reaction equation

HRID 2112109 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[C:16](=[O:18])[NH:15][C:14]2([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:29][CH2:30][F:31].[H-].[Na+]>C(OCC)(=O)C>[CH2:21]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[C:16](=[O:18])[N:15]([CH2:29][CH2:30][F:31])[C:14]2([CH3:20])[CH3:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 670947987-Dibenzylamino-3,3-dimethyl-2,3-dihydro-isoindol-1-one

Product 1

HCID 866061867-Dibenzylamino-2-(2-fluoro-ethyl)-3,3-dimethyl-2,3-dihydro-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

67 mg (0.188 mmol) 7-dibenzylamino-3,3-dimethyl-2,3-dihydro-isoindol-1-one are dissolved in 1 ml (7.877 mmol) 1-bromo-2-fluoroethane and combined with 52 mg (0.376 mmol) sodium hydride. After 4 h stirring at ambient temperature the mixture is diluted with ethyl acetate and extracted three times with 1 M hydrochloric acid. The combined organic phases are dried and the solvent is eliminated in vacuo.

Workup

  1. extractionextracted three times with 1 M hydrochloric acid
  2. customThe combined organic phases are dried

Sources & evidence

ORD record
ord-356bfbeddf0c41f2b6c802b2c794c6ad
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

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