Cesium carbonate → HCID 86710155, compound

HRID 705363Notes

Reaction equation

HRID 705363 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21](I)[CH2:22][CH:23]([CH3:25])[CH3:24]>CN(C)C=O.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[S:11]([CH3:14])(=[O:12])=[O:13])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 109241-Iodo-3-methylbutaneHCID 69672723HCID 69672723, compound

Product 1

HCID 86710155HCID 86710155, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Example 17F (814 mg, 3.83 mmol) and cesium carbonate (1.87 g, 5.75 mmol) in N,N-dimethylformamide was treated with isoamyl iodide (555 μL, 835 mg, 4.22 mmol) followed by stirring at room temperature for 48 hours. The mixture was diluted with ethyl acetate and extracted with water (3×) and saturated sodium chloride solution. Drying (Na2SO4) and concentration in vacuo afforded an amber oil, which was chromatographed over a 50 g silica gel cartridge, eluting with 15-70% ethyl acetate in dichloromethane. These procedures afforded the product (474 mg, 44%) as an off-white solid.

Workup

  1. extractionextracted with water (3×) and saturated sodium chloride solution
  2. customDrying
  3. concentration(Na2SO4) and concentration in vacuo
  4. customafforded an amber oil, which
  5. customwas chromatographed over a 50 g silica gel cartridge
  6. washeluting with 15-70% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-a9eb889d7d8a46b0aa43dfe671e0c9ab
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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