Dimethylformamide → HCID 66974436, compound

HRID 1782372Notes

Reaction equation

HRID 1782372 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([S:21]([C:24]2[CH:25]=[N:26][CH:27]=[C:28](Br)[CH:29]=2)(=[O:23])=[O:22])[CH:11]=1)C)(C)(C)C.[CH3:32][N:33](C)C=O.C(OCC)(=O)C.[ClH:43]>C(O)C.[C-]#N.[Zn+2].[C-]#N>[ClH:43].[CH3:6][NH:7][CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]([S:21]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:29]=2)[C:32]#[N:33])(=[O:22])=[O:23])[CH:11]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974640HCID 66974640, compound

Product 1

HCID 66974436HCID 66974436, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl({1-[(5-bromopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate (112 mg), zinc cyanide (50 mg) and N,N-dimethylformamide (4 mL) was degassed with argon gas. Tetrakis(triphenylphosphine)palladium (46 mg) was added, and the mixture was stirred at 100 degree C. for 1.5 hr. After cooling the reaction mixture to room temperature, a saturated aqueous sodium-hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:2) to give a colorless oil. The obtained oil was dissolved in ethanol (2 mL), and a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added. After stirring at room temperature for 1 hr, the mixture was concentrated under reduced pressure, and recrystallized from ethanol to give the title compound as a solid (yield 32.7 mg, 42%).

Workup

  1. customwas degassed with argon gas
  2. additionTetrakis(triphenylphosphine)palladium (46 mg) was added
  3. additiona saturated aqueous sodium-hydrogencarbonate solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→3:2)
  9. customto give a colorless oil
  10. stirringAfter stirring at room temperature for 1 hr
  11. concentrationthe mixture was concentrated under reduced pressure
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-94e31daf15374fc184a1963d777b0026
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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