Acetone → HCID 58415471, compound

HRID 46173Notes

Reaction equation

HRID 46173 reaction equation
[CH2:1]([C:8]1([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH3:32][C:33]([CH3:35])=[O:34]>C1COCC1>[CH2:1]([C:8]1([C:20]2[CH:25]=[CH:24][C:23]([C:33]([OH:34])([CH3:35])[CH3:32])=[CH:22][CH:21]=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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 462065995-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindoleHCID 178418339Butyllithium

Product 1

HCID 58415471HCID 58415471, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of 5-benzyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (100 mg) in THF (3 mL) was cooled to −78° C. and n-BuLi solution (0.234 mL, 1.6 M in hexane) was added slowly. After stirring for 10 minutes acetone (29 mg) was added to the resulting red solution. After 30 min of the addition of acetone, reaction was quenched with aqueous saturated NH4Cl. The reaction mixture was partitioned between saturated aqueous NH4Cl and EtOAc.

Workup

  1. additionwas added to the resulting red solution
  2. customwas quenched with aqueous saturated NH4Cl
  3. customThe reaction mixture was partitioned between saturated aqueous NH4Cl and EtOAc

Sources & evidence

ORD record
ord-b124a95cab3e49e289e30ce845b760a1
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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