Potassium Iodide → HCID 11510788, compound

HRID 1445824Notes

Reaction equation

HRID 1445824 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C@H:17]3[CH3:21])=O)[N:12]=2)=[CH:4][CH:3]=1.[CH3:23][S:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1)(=[O:26])=[O:25].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+]>CN(C=O)C>[CH3:23][S:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]([CH3:22])=[C:11]([CH2:13][CH2:14][N:16]4[CH2:20][CH2:19][CH2:18][C@H:17]4[CH3:21])[N:12]=3)=[CH:4][CH:3]=2)=[CH:29][CH:28]=1)(=[O:25])=[O:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 135487319HCID 135487319, compound

Product 1

HCID 11510788HCID 11510788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[2-(4-Hydroxy-phenyl)-5-methyl-oxazol-4-yl]-1-(2-(R)-methyl-pyrrolidin-1-yl)-ethanone (See Example 56) (0.32 g, 1.1 mmol), 4-methylsulfonylbenzyl chloride (0.29 g, 1.4 mmol), Cs2CO3 (0.9 g, 2.75 mmol), and potassium iodide (0.24 g, 1.4 mmol) in DMF (5 mL) is stirred at room temperature overnight. The mixture is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc (2×), and the combined organic phase is washed with brine, dried (Na2SO4), and concentrated. The residue is purified by flash chromatography [40 g SiO2, elute 20% (10% 2 M NH3 in MeOH/90% CH2Cl2): 80% CH2Cl2 to 70% (10% 2 M NH3 in MeOH/90% CH2Cl2): 30% CH2Cl2] to yield the title compound. MS (m/e): 455.3 (M+1)

Workup

  1. customThe mixture is partitioned between EtOAc and water
  2. extractionThe aqueous phase is extracted with EtOAc (2×)
  3. washthe combined organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography [40 g SiO2, elute 20% (10% 2 M NH3 in MeOH/90% CH2Cl2): 80% CH2Cl2 to 70% (10% 2 M NH3 in MeOH/90% CH2Cl2): 30% CH2Cl2]

Sources & evidence

ORD record
ord-58dbf7aa7cf84e558a521e393b641619
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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