Benzyl Bromide → 5-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole

HRID 46164Notes

Reaction equation

HRID 46164 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.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.C1CCCCC1>[CH2:20]([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)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 7498Benzyl Bromide2×HCID 584155145-(4-Bromophenyl)-5H-imidazo[2,1-A]isoindole

Product 1

HCID 462065995-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (5 g) in THF (100 mL) at −78° C. was added LAD solution (21.42 mL, 1.5 M in cyclohexane). After stirring for 15 minutes benzylbromide was added and the reaction mixture was stirred at −40° C. After 20 minutes more benzylbromide (3 mL) was added and continued to stir at −40° C. for 40 minutes. The reaction was then quenched with aqueous saturated NH4Cl and partitioned between aqueous saturated NH4Cl and EtOAc. Aqueous layer was extracted with EtOAc (2×). Combined organic layers were dried over Na2SO4 and concentrated. The resulting yellow solid was recrystallized from hot EtOAc to yield title compound as a white solid. HRMS. Found, 401.0647; calcd for (M+H)+, 401.0648. 1HNMR (500 MHz, CDCl3): δ 7.62 (d, J=7.1 Hz, 1H), 7.50 (d, J=8.6 Hz, 2H), 7.36 (dd, J=7.1, 0.9 Hz, 1H), 7.33-7.27 (m, 2H), 7.24 (s, 1H), 7.15 (d, J=8.3 Hz, 2H), 7.03 (t, J=7.8 Hz, 1H), 6.95 (t, J=7.8 Hz, 2H), 6.91 (s, 1H), 6.56 (d, J=7.6 Hz, 2H), 3.78 (s, 2H).

Workup

  1. additionwas added
  2. stirringto stir at −40° C. for 40 minutes
  3. customThe reaction was then quenched with aqueous saturated NH4Cl
  4. custompartitioned between aqueous saturated NH4Cl and EtOAc
  5. extractionAqueous layer was extracted with EtOAc (2×)
  6. dry with materialCombined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe resulting yellow solid was recrystallized from hot EtOAc

Sources & evidence

ORD record
ord-56cc84fb91e148c6b96670f9e9b5dbf6
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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