Sodium hydride → 4-Bromo-1-[(3-fluorophenyl)methyl]-1H-indole-2,3-dione

HRID 730580Notes

Reaction equation

HRID 730580 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[NH:6]2.[H-].[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Br>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[N:6]2[CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[C:16]([F:15])[CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 45000124-Bromoisatin

Product 1

HCID 284924774-Bromo-1-[(3-fluorophenyl)methyl]-1H-indole-2,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromo-1H-indole-2,3-dione (6.38 g) was dissolved in 100 mL of DMF and at 0° C., and 60% NaH (1.32 g) was added in portions. The mixture was stirred for 20 minutes before adding 3-fluorobenzyl bromide. The solution was stirred for approximately 30 minutes, quenched with water, and partitioned between water and diethyl ether. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to yield 9.18 g 4-Bromo-1-(3-fluoro-benzyl)-1H-indole-2,3-dione that was sufficiently pure for use in step 2 below. MS: 385 (M+H)+.

Workup

  1. stirringThe solution was stirred for approximately 30 minutes
  2. customquenched with water
  3. custompartitioned between water and diethyl ether
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-69e001a7783d40b59848501397b28cb7
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

Loading…