Sodium Iodide → HCID 11857527, compound

HRID 1710743Notes

Reaction equation

HRID 1710743 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([CH2:17][C:18](=[O:24])[N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:16]=2)=[CH:8][CH:7]=1.[I-].[Na+].[CH3:27][CH:28]1[CH2:32][CH2:31][CH2:30][NH:29]1.ClCCl>C(#N)C>[CH3:27][CH:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][CH:14]=[C:15]([CH2:17][C:18](=[O:24])[N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[N:16]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6344DichloromethaneHCID 130032-MethylpyrrolidineHCID 59457512HCID 59457512, compound

Product 1

HCID 11857527HCID 11857527, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-[4-(3-chloropropoxy)phenyl]-4-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-oxazole ax64 (0.51 g, 1.46 mmol, 1 eq) in acetonitrile (10 ml) is added sodium iodide (0.022 g, 0.15 mmol, 0.1 eq) and 2-methylpyrrolidine (0.25 ml, 2.92 mmol, 2 eq). The mixture is stirred at reflux overnight. The mixture is poured into dichloromethane and washed with water. The organic layer is dried over magnesium sulfate and the solvent is removed under vacuum. The crude product is purified by chromatography over silica gel (eluent: dichloromethane/methanol/ammonia 95:4.5:0.5) to give 0.29 g of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-oxazole 52 as a yellow oil.

Workup

  1. temperatureat reflux overnight
  2. washwashed with water
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. customthe solvent is removed under vacuum
  5. customThe crude product is purified by chromatography over silica gel (eluent: dichloromethane/methanol/ammonia 95:4.5:0.5)

Sources & evidence

ORD record
ord-5243c1bb543d4bba8d53bd92b5bcf508
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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