1,1-Dibromoethane → HCID 68735645, compound

HRID 529128Notes

Reaction equation

HRID 529128 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:23]=[CH:22][C:8]([CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]#[N:20])[C:13]=3[CH2:12][C:11]2=[O:21])=[CH:7][CH:6]=1.Br[CH:25](Br)[CH3:26]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]#[N:20])[C:13]=3[C:12]3([CH2:26][CH2:25]3)[C:11]2=[O:21])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 24758Sodium hydride2×HCID 68735617HCID 68735617, compound

Product 1

HCID 68735645HCID 68735645, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (0.457 g, 19.0 mmol) was added to a solution of 1-(4-methoxybenzyl)-2-oxoindoline-4-carbonitrile (5.30 g, 19.0 mmol) in DMF (38 mL), and the resulting slurry was stirred at ambient temperature for 1 hour. Dibromoethane (3.94 g, 21.0 mmol) was then added to this mixture, and the mixture was stirred at room temperature for 1 hour. An additional equivalent of NaH (0.457 g, 19.0 mmol) was then added to the reaction mixture, and the reaction was stirred at 80° C. for 3 hours. The reaction mixture was concentrated and purified by column chromatography with a hexanes/ethyl acetate gradient +15% DCM. The mixed product fractions were recrystallized with DCM/hexanes to give 1′-(4-methoxybenzyl)-2′-oxospiro[cyclopropane-1,3′-indoline]-4′-carbonitrile (5.00 g, 16.4 mmol, 86%). LCMS (APCI+) M+H+ 305 (100%); Rt=3.65 min.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. stirringthe reaction was stirred at 80° C. for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography with a hexanes/ethyl acetate gradient +15% DCM
  5. customThe mixed product fractions were recrystallized with DCM/hexanes

Sources & evidence

ORD record
ord-7e41c212fe974fe3bb07a46edeedc719
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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