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Dimethylformamide → HCID 68663454, compound

HRID 452794
Notes
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Reaction equation

HRID 452794 reaction equation
Br[C:2]1[C:6]2[CH:7]=[C:8]([C:11]3[O:12][C:13]([CH3:16])=[N:14][N:15]=3)[CH:9]=[CH:10][C:5]=2[O:4][CH:3]=1.[CH3:17][N:18](C)C=O>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>[CH3:16][C:13]1[O:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]3[O:4][CH:3]=[C:2]([C:17]#[N:18])[C:6]=3[CH:7]=2)=[N:15][N:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 444806972-(3-Bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole

Product 1

HCID 68663454HCID 68663454, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compound
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-(3-bromo-1-benzofuran-5-yl)-5-methyl-1,3,4-oxadiazole (5.58 g, 20.0 mmol), zinc cyanide (1.41 g, 12.0 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.16 g, 1.00 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. for 10 hr under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed twice with water and once with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (3.74 g, yield 83%) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. washwashed twice with water and once with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  6. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-0069a782a0c14c03a25de0fcdee9280c
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492378B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes