Boron tribromide → HCID 58415420, compound

HRID 46180Notes

Reaction equation

HRID 46180 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:22][CH2:23][C:24]([N:26]3[CH:30]([CH3:31])[CH2:29][CH2:28][CH:27]3[CH3:32])=[O:25])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17]C)[C:10]3=[N:19][CH:20]=[CH:21][N:9]23)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:22][CH2:23][C:24]([N:26]3[CH:30]([CH3:31])[CH2:29][CH2:28][CH:27]3[CH3:32])=[O:25])[C:16]3[C:15]([OH:17])=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3=[N:19][CH:20]=[CH:21][N:9]23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 584154575-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-6-methoxy-5H-imidazo[2,1-a]isoindole

Product 1

HCID 58415420HCID 58415420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-5-[3-(2,5-dimethylpyrrolidin-1-yl)-3-oxopropyl]-6-methoxy-5H-imidazo[2,1-a]isoindole (190 mg) in CH2Cl2 (2 mL) was added BBr3 (1.7 ml) slowly at 0° C. After 90 min the mixture was quenched with saturated aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to an off-white solid (179 mg) which was sufficiently pure for use in the next step.

Workup

  1. customAfter 90 min the mixture was quenched with saturated aqueous NaHCO3
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to an off-white solid (179 mg) which

Sources & evidence

ORD record
ord-b236ca9cc9ab40e18a269a57690a469a
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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