Benzyl Bromide → HCID 10660235, compound

HRID 1158727Notes

Reaction equation

HRID 1158727 reaction equation
[CH3:1][N:2](/[CH:4]=[C:5]1\[C:6](=[O:14])[NH:7][C:8]2[C:13]\1=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:3].[H-].[Na+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[CH2:17]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)/[C:5](=[CH:4]/[N:2]([CH3:1])[CH3:3])/[C:6]1=[O:14])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 728912HCID 728912, compound

Product 1

HCID 10660235HCID 10660235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3Z)-3-[(dimethylamino)methylene]-1,3-dihydro-2H-indol-2-one (iii-a, 626 mg, 3.33 mmol) in DMF (10 mL) was added NaH (151 mg, 6.29 mmol) and the reaction was stirred at RT. After 10 min, benzyl bromide (500 μL, 4.20 mmol) was added and the mixture was stirred under an atmosphere of Ar for 22 h. The reaction was quenched with a few drops of water and poured into a separatory funnel containing EtOAc (150 mL) and washed with water (2×100 mL), followed by brine (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (EtOAc/Hexane) to yield (3Z)-1-benzyl-3-[(dimethylamino)methylene]-1,3-dihydro-2H-indol-2-one as a yellow solid (iv-a, 660 mg, 71%). NH4OAc QC conditions. DAD Retention Time =1.71 min. M+H=279.

Workup

  1. stirringthe mixture was stirred under an atmosphere of Ar for 22 h
  2. customThe reaction was quenched with a few drops of water
  3. additionpoured into a separatory funnel
  4. additioncontaining EtOAc (150 mL)
  5. washwashed with water (2×100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-29b548b3ab564986a57ee3dc9c0037f7
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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