tert-Butyl bromoacetate → HCID 58415621, compound

HRID 46166Notes

Reaction equation

HRID 46166 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3=[N:17][CH:18]=[CH:19][N:9]23)=[CH:4][CH:3]=1.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>C1COCC1.C1CCCCC1>[C:25]([O:24][C:22](=[O:23])[CH2:21][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2=[N:17][CH:18]=[CH:19][N:9]12)([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 584155145-(4-Bromophenyl)-5H-imidazo[2,1-A]isoindole

Product 1

HCID 58415621HCID 58415621, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of 5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (3.17 g) in THF (60 mL) at −78° C. was added LAD solution (10.19 mL, 1.5 M in cyclohexane) drop wise. After stirring for 5 minutes tert-butyl bromoacetate was added, cooling bath was removed and the reaction mixture was stirred at room temperature. After 1.5 h the reaction was quenched with aqueous saturated NH4Cl and layers were separated. Aqueous layer was extracted with EtOAc (2×). Combined organic layers were dried over Na2SO4 and concentrated. Flash chromatography using a linear gradient of 1-50% EtOAc in hexanes afforded title compound as a white solid. Mass. found (M+H)+, 427.0.

Workup

  1. additionwas added
  2. temperaturecooling bath
  3. customwas removed
  4. customAfter 1.5 h the reaction was quenched with aqueous saturated NH4Cl and layers
  5. customwere separated
  6. extractionAqueous layer was extracted with EtOAc (2×)
  7. dry with materialCombined organic layers were dried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c2442bf4b791480ea2b180a4e10d079c
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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