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HCID 86630998, compound → HCID 86631001, compound

HRID 1782327
Notes
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Reaction equation

HRID 1782327 reaction equation
Br[C:2]1[N:3]([S:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[CH:5][C:6]=1[CH:7]=[O:8].[Cu][C:26]#[N:27]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:4]1[N:3]([S:16]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[C:2]([C:26]#[N:27])=[C:6]([CH:7]=[O:8])[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 86630998HCID 86630998, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86631001HCID 86631001, compoundYield 57.2%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Procedure

2-Bromo-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde (340 mg), copper (I) cyanide (400 mg), tris(dibenzylideneacetone)dipalladium (0) (40 mg), 1,1′-bis(diphenylphosphino)ferrocene (70 mg) were mixed in 1,4-dioxane (30 mL), and the mixture was heated under reflux for 24 hr. The reaction mixture was allowed to cool, diluted with ethyl acetate, and filtered. The obtained filtrate was washed with a saturated aqueous sodium hydrogencarbonate solution and 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=3:2) and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 169 mg, 57%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. temperatureto cool
  4. filtrationfiltered
  5. washThe obtained filtrate was washed with a saturated aqueous sodium hydrogencarbonate solution and 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=3:2)
  9. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e9f38a1d417242f580b090c5ec4ba0d7
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07498337B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes