Benzyl Bromide → HCID 11086219, compound

HRID 2246735Notes

Reaction equation

HRID 2246735 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:12])([CH3:1])[C:3]1=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 11086219HCID 11086219, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,3-Dimethyl-1,3-dihydro-indol-2-one (5.5 g, 34 mmol) was dissolved in dimethylformamide (50 mL) and sodium hydride (1.4 g, 38 mmol) was added portionwise and the mixture was stirred 30 minutes then benzyl bromide (4.8 mL, 41 mmol) was added. The mixture was stirred 2 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 7.1 g (83%) of 1-benzyl-3,3-dimethyl-1,3-dihydro-2H-indol-2-one.

Workup

  1. stirringThe mixture was stirred 2 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-894d1994d8e14948867ad1e7144cc5b8
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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