Dimethylformamide → HCID 57522481, compound

HRID 1962641Notes

Reaction equation

HRID 1962641 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][C:27]([Cl:30])=[CH:28][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.Cl>C(OCC)(=O)C.[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>[ClH:30].[CH3:6][NH:7][CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:12]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([C:32]#[N:33])=[N:26][CH:25]=2)(=[O:22])=[O:23])[CH:11]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 21866389Hydrogen chloride-ethyl acetateHCID 86620796HCID 86620796, compound

Product 1

HCID 57522481HCID 57522481, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere, a mixture of tert-butyl{[1-(6-chloro-3-pyridinesulfonyl)-5-phenyl-1H-pyrrol-3-yl]methyl}methylcarbamate (100 mg), zinc (II) cyanide (51 mg), tetrakis(triphenylphosphine)palladium (50 mg) and N,N-dimethylformamide (4 mL) was stirred at 100° C. for 2 hr. The reaction mixture was diluted with ethyl acetate, washed successively with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→7:3) to give an oil. The obtained oil was dissolved in ethyl acetate (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 solvent was evaporated under reduced pressure, and the residue was crystallized from ethanol to give the title compound (yield 57 mg, 68%).

Workup

  1. washwashed successively with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=19:1→7:3)
  5. customto give an oil
  6. stirringAfter stirring at room temperature for 1 hr
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-b98f856656f641899e8b8392b77b4da0
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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