Cesium carbonate → HCID 86603572, compound

HRID 1820842Notes

Reaction equation

HRID 1820842 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:23].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:23][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 68982158HCID 68982158, compound

Product 1

HCID 86603572HCID 86603572, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (356 mg, 0.931 mmol), prepared in step 1 of Example 3, methyl bromoacetate (106 μL, 1.12 mmol) and cesium carbonate (457 mg, 1.40 mmol) in 25 mL of acetone was stirred under nitrogen at room temperature for 19 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted multiple times with methylene chloride. The combined organic extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give methyl {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetate (401 mg, 95%) as an off-white solid, mp 156-159° C. Elemental Analysis for C22H16BrNO3S Calc'd: C, 58.16; H, 3.55; N, 3.08. Found: C, 57.87; H, 3.43; N, 2.94.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customto remove the acetone
  3. customThe residue was partitioned between methylene chloride and water
  4. customThe aqueous layer was separated
  5. extractionextracted multiple times with methylene chloride
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-154d1fe2704049a6a24bd5f19f7c6506
Source dataset
uspto-grants-2009_10
Patent number
US07605172B2

Reaction notes

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