Sodium hydride → HCID 68528429, compound

HRID 2246730Notes

Reaction equation

HRID 2246730 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2([CH3:13])[CH3:12].[H-].[Na+].[F:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([F:16])[CH:18]=1)[C:8](=[O:11])[C:7]2([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680073-Fluorobenzyl bromideHCID 119764367-fluoro-3,3-dimethyloxindole

Product 1

HCID 68528429HCID 68528429, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.3 g, 7.3 mmol) was dissolved in dimethylformamide (14 mL) and NaH (0.30 g, 8 mmol) was added and the mixture was stirred 30 minutes then 3-fluorobenzyl bromide (1.5 g, 8.0 mmol) was added. The mixture was stirred 4 hours then quenched with saturated aqueous ammonium chloride, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 0-20% ethyl acetate in hexane) to afford 1.7 g (81%) of 7-fluoro-1-(3-fluorobenzyl)-3,3-dimethyl-1,3-dihydro-2H-indol-2-one.

Workup

  1. stirringThe mixture was stirred 4 hours
  2. customthen quenched with saturated aqueous ammonium chloride
  3. additiondiluted with ether
  4. washwashed with water, and saturated brine
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-180a3d69a4d040a8929ebf243e33168b
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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