Water → HCID 59322925, compound

HRID 331244Notes

Reaction equation

HRID 331244 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:10]2[C:13]3[C:3]=1[CH2:4][CH:5]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:16][CH2:15]1)[C:6]=3[CH:7]=[CH:8][CH:9]=2.O.C(OCC)(=O)C.[CH3:37][N:38](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:37]([C:2]1[CH:12]=[CH:11][C:10]2[C:13]3[C:3]=1[CH2:4][CH:5]([N:14]1[CH2:15][CH2:16][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[NH:22][C:21]4=[O:29])[CH2:18][CH2:19]1)[C:6]=3[CH:7]=[CH:8][CH:9]=2)#[N:38]

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 59322930HCID 59322930, compound

Product 1

HCID 59322925HCID 59322925, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
110 °C

Procedure

1-[1-(3-Bromoacenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one (1.25 g) was dissolved in N,N-dimethylformamide (16 ml), zinc cyanide (380 mg) and tetrakistriphenylphosphinepalladium (1.6 g) were added, and the mixture was stirred at 110° C. for 1 hr. After allowing to cool, water and ethyl acetate were poured into the reaction mixture, and the mixture was subjected to celite filtration. The filtrate was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography, and recrystallized from acetone to give the title compound (1.0 g).

Workup

  1. temperatureto cool
  2. filtrationthe mixture was subjected to celite filtration
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-fab7353795c144318120c167b3b7c936
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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