Sodium Carbonate → HCID 58963165, compound

HRID 917528Notes

Reaction equation

HRID 917528 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:15]2[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]([O:23][CH2:24][CH:25]=[CH2:26])=[C:17](Br)[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[Na+].[Na+].C(O[Na])=O.[NH4+].[Cl-]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(N(C)C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:15]2[CH:20]=[C:19]([CH2:21][CH3:22])[C:18]3[O:23][CH:24]=[C:25]([CH3:26])[C:17]=3[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 58963168HCID 58963168, compoundHCID 178526064HCID 178526064, compound

Product 1

HCID 58963165HCID 58963165, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

Following the general procedure of Larock et al (Tetrahedron Lett, 1988, 29:4687), a mixture of methyl 2-(4-cyanophenylamino)-2-(4-(allyloxy)-3-bromo-5-ethylphenyl)acetate 4 (5.00 g, 11.7 mmol), Na2CO3 (3.09 g, 29.1 mmol), HCO2Na (800 mg, 11.7 mmol), Bu4N+C− (3.56 g, 12.8 mmol) and DMA was degassed by bubbling N2 for 1 h. Palladium(II) acetate (130 mg, 0.58 mmol) was added, the flask was sealed with a glass stopper and heated at 80° C. for 19 h. The mixture was poured into ½-saturated NH4Cl (500 mL) and extracted with diethylether (Et2O, 4×125 mL). The combined organic layers were washed with saturated NH4Cl (1×125 mL), water (1×125 mL), brine (1×125 mL), dried over magnesium sulfate (MgSO4), filtered, and concentrated. The residue was adsorbed onto Celite®, then purified by silica gel chromatography (SiO2, gradient elution 10–15–20% ethyl acetate/hexanes) to yield 1.11 g (27%) of methyl 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetate 5 as a colorless solid.

Workup

  1. customwas degassed
  2. customby bubbling N2 for 1 h
  3. customthe flask was sealed with a glass stopper
  4. extractionextracted with diethylether (Et2O, 4×125 mL)
  5. washThe combined organic layers were washed with saturated NH4Cl (1×125 mL), water (1×125 mL), brine (1×125 mL)
  6. dry with materialdried over magnesium sulfate (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (SiO2, gradient elution 10–15–20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-192eb104ef4445e09bf5662e025ddda0
Source dataset
uspto-grants-2007_09
Patent number
US07273886B2

Reaction notes

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