Sodium Carbonate → HCID 13491715, compound

HRID 2060849Notes

Reaction equation

HRID 2060849 reaction equation
I[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].C[C:21]([N:23](C)C)=O>CCOC(C)=O.[Fe-4](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[K+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][CH:3]=[C:2]2[C:21]#[N:23]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 123363951-Iodo-5-methoxynaphthalene

Product 1

HCID 13491715HCID 13491715, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178511492HCID 178511492, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-iodo-5-methoxynapthalene (J. A. O'Meara et al., J. Med. Chem., 2005, 48, 5580-5588 1.104 g, 3.89 mmol) in dimethylacetamide (6 mL) at rt under nitrogen, was added potassium ferrocyanide (494 mg, 1.17 mmol), Na2CO3 (412 mg, 3.89 mmol) and palladium acetate (43 mg, 0.19 mmol). The reaction mixture was stirred at 120° C. for 3 h, cooled, diluted with EtOAc (100 mL) and filtered through Celite. The organic phase was washed with water (30 mL), NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (isohexane:EtOAc, 90:10 to 85:15) to give the title compound: RT=3.64 min; m/z (ES+)=184.0 [M+H]+.

Workup

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. washThe organic phase was washed with water (30 mL), NaHCO3 (30 mL), brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. customSolvent was removed in vacuo
  6. customthe residue purified by column chromatography (isohexane:EtOAc, 90:10 to 85:15)

Sources & evidence

ORD record
ord-be936232271f4123b9996975867d60e7
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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