Dimethylformamide → HCID 66974649, compound

HRID 1782357Notes

Reaction equation

HRID 1782357 reaction equation
Br[C:2]1[C:3]([C:7]2[N:11]([S:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:8]=2)=[CH:4][S:5][CH:6]=1.[CH3:31][N:32](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:31]([C:2]1[C:3]([C:7]2[N:11]([S:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:21][N:22]([CH3:30])[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:8]=2)=[CH:4][S:5][CH:6]=1)#[N:32]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 66974586tert-butyl{[5-(4-bromo-3-thienyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Product 1

HCID 66974649HCID 66974649, compoundYield 71%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

To a solution (5 mL) of tert-butyl {[5-(4-bromo-3-thienyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (470 mg) in N,N-dimethylformamide were added zinc cyanide (215 mg) and tetrakis(triphenylphosphine)palladium (212 mg) and the mixture was sufficiently degassed. The mixture was stirred with heating at 120° C. for 18 hr and cooled to room temperature. Water and ethyl acetate were added and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:1) to give the title compound as a pale-yellow oil (yield 297 mg, 71%).

Workup

  1. customthe mixture was sufficiently degassed
  2. temperaturecooled to room temperature
  3. additionWater and ethyl acetate were added
  4. filtrationthe mixture was filtered through celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-e4e1353da35943b5aed4126e8a4a3946
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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