Potassium Carbonate → HCID 25059296, compound

HRID 331245Notes

Reaction equation

HRID 331245 reaction equation
C[O:2][C:3]1[C:13]2[C:14]3[C:6]([CH2:7][CH:8]([N:15]4[CH2:20][CH2:19][CH:18]([N:21]5[C:25]6[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=6[N:23]([CH2:30][C:31]([NH:33][CH3:34])=[O:32])[C:22]5=[O:35])[CH2:17][CH2:16]4)[C:9]=3[CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CC(C)=O>[OH:2][C:3]1[C:13]2[C:14]3[C:6]([CH2:7][CH:8]([N:15]4[CH2:16][CH2:17][CH:18]([N:21]5[C:25]6[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=6[N:23]([CH2:30][C:31]([NH:33][CH3:34])=[O:32])[C:22]5=[O:35])[CH2:19][CH2:20]4)[C:9]=3[CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 25059295HCID 25059295, compound

Product 1

HCID 25059296HCID 25059296, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

2-{3-[1-(5-Methoxyacenaphthen-1-yl)piperidin-4-yl]-2,3-dihydro-2-oxo-benzimidazol-1-yl}-N-methylacetamide (780 mg) was dissolved in dichloromethane (50 ml), a solution (8.0 ml) of boron tribromide (1.0 mol) in dichloromethane was added dropwise under a nitrogen stream while cooling to −50° C., and the mixture was gradually warmed over 1 hr. After completion of the reaction, the reaction mixture was poured into an aqueous potassium carbonate solution by small portions, during which unnecessary substances were dissolved in acetone), the mixture was extracted with chloroform, and the extract was dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by NH-coating silica gel column chromatography to give a crude product of the title compound.

Workup

  1. temperaturethe mixture was gradually warmed over 1 hr
  2. customAfter completion of the reaction
  3. extractionwas extracted with chloroform
  4. dry with materialthe extract was dried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by NH-coating silica gel column chromatography

Sources & evidence

ORD record
ord-1e1f1ae7eab0463894e1e4c8aeae8fe6
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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