Sodium Iodide → HCID 59457488, compound

HRID 1710760Notes

Reaction equation

HRID 1710760 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH:13]=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[N:15]=2)=[CH:7][CH:6]=1.[CH3:21][CH:22]1[CH2:26][CH2:25][CH2:24][NH:23]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:21][CH:22]1[CH2:26][CH2:25][CH2:24][N:23]1[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:12][CH:13]=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[N:15]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457508HCID 59457508, compound

Product 1

HCID 59457488HCID 59457488, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl {2-[4-(2-chloroethoxy)phenyl]-1,3-oxazol-4-yl}acetate 151 (0.55 g, 1.86 mmol, 1 eq) is reacted with 2-methylpyrrolidine (0.28 ml, 2.79 mmol, 1.5 eq) in the presence of potassium carbonate (0.77 g, 5.58 mmol, 3 eq) and a catalytic quantity of sodium iodide in refluxing acetonitrile (20 ml). After 45 h, the solvent is evaporated, the residue is then taken up in ethyl acetate and washed two times with an aqueous solution of sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 97:2.7:0.3) affords 0.3 g of methyl (2-{4-[2-(2-methylpyrrolidin-1-yl)ethoxy]phenyl}-1,3-oxazol-4-yl)acetate i52.

Workup

  1. customthe solvent is evaporated
  2. washwashed two times with an aqueous solution of sodium hydrogenocarbonate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification by chromatography over silicagel (eluent: dichloromethane/methanol/ammonia 97:2.7:0.3)

Sources & evidence

ORD record
ord-14ae0ed03aef42bc8e7e8917aa29dfdd
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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