Sodium Carbonate → HCID 67198154, compound

HRID 547281Notes

Reaction equation

HRID 547281 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].[O:18]1[CH:22]=[CH:21][N:20]=[C:19]1B(O)O>C1COCC1>[O:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:2]1[CH:3]=[C:4]([CH:8]([CH3:11])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 601460961,3-Oxazol-2-ylboronic acidHCID 67201174HCID 67201174, compound

Product 1

HCID 67198154HCID 67198154, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-iodophenyl)propionitrile (0.6 g, 2.33 mmol) in dry THF (10 mL) Pd(PPh3)4 (4% mol, 0.108 mg) and Na2CO3 (0.493 g, 4.66 mmol) were added sequentially under nitrogen atmosphere. After stirring 20 min commercial 1,3-oxazole-2-boronic acid (0.289 g 2.56 mmol) was added. The reaction mixture was stirred at reflux 4 h. After cooling at room temperature, THF was evaporated under reduced pressure and EtOAc (10 mL) was added to the crude and the organic phase was washed with water (3×10 mL) and brine (3×10 mL). After drying over Na2SO4 and solvent evaporation a residue was obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 8:2), afforded 2-(3-oxazol-2-ylphenyl) propionitrile as yellow oil (0.360 g, 1.82 mmol). Yield 78%.

Workup

  1. additionwas added
  2. temperatureat reflux 4 h
  3. customTHF was evaporated under reduced pressure and EtOAc (10 mL)
  4. additionwas added to the crude
  5. washthe organic phase was washed with water (3×10 mL) and brine (3×10 mL)
  6. dry with materialAfter drying over Na2SO4 and solvent evaporation a residue
  7. customwas obtained that, after flash chromatography (eluent mixture n-hexane/EtOAc 8:2)

Sources & evidence

ORD record
ord-d452775ef3504ba48987e11a849336fd
Source dataset
uspto-grants-2011_05
Patent number
US07939521B2

Reaction notes

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