Sodium Iodide → HCID 18445373, compound

HRID 460031Notes

Reaction equation

HRID 460031 reaction equation
C[Si](Cl)(C)C.[I-].[Na+].C(#N)C.O[CH:12]([C:31]1[CH:43]=[CH:42][C:34]([O:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:33]([CH3:44])[CH:32]=1)[CH2:13][CH2:14][C:15]1[S:19][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH3:30]>C1CCCCC1>[CH2:40]([O:39][C:37](=[O:38])[CH2:36][O:35][C:34]1[CH:42]=[CH:43][C:31]([CH2:12][CH2:13][CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:24][CH:25]=3)=[N:17][C:16]=2[CH3:30])=[CH:32][C:33]=1[CH3:44])[CH3:41]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 86592484HCID 86592484, compound2×

Product 1

HCID 18445373HCID 18445373, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
21 °C

Procedure

To a stirred mixture of trimethylsilylchloride (0.15 ml), sodium iodide (0.175 g) and acetonitrile (0.061 ml) was added a solution of ethyl [4-(1-hydroxy-3-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}propyl)-2-methylphenoxy]acetate (intermediate 12, 0.096 g) in cyclohexane (1 ml). The reaction mixture was stirred at 21° C. for 18 hours and then refluxed for 2 hours. The reaction mixture was partitioned between water and ethyl acetate; the aqueous layer separated and extracted twice more with ethyl acetate. The organic solutions were combined and were dried with brine and over magnesium sulfate and concentrated. The product isolated after evaporation of the solvent was further purified by flash chromatography using cyclohexane: ethyl acetate (7:1) as eluent to give the title compound as a pale yellow gum.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customthe aqueous layer separated
  4. extractionextracted twice more with ethyl acetate
  5. dry with materialwere dried with brine and over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product isolated
  8. customafter evaporation of the solvent
  9. customwas further purified by flash chromatography

Sources & evidence

ORD record
ord-8dc5ca12efdd40d1bc812d3f182d22af
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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