Cesium carbonate → HCID 86603521, compound

HRID 2355127Notes

Reaction equation

HRID 2355127 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[CH:22]=[C:21]([OH:26])[CH:20]=[CH:19]4)=[CH:14][N:15]=2)=[CH:3]1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[CH:22]=[C:21]([O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:20]=[CH:19]4)=[CH:14][N:15]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 68451243HCID 68451243, compound

Product 1

HCID 86603521HCID 86603521, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-[2-(1-methyl-1H-indol-3-yl)-oxazol-5-yl]-naphthalen-2-ol (289 mg, 0.843 mmol), prepared in step 4 of Example 8, methyl bromoacetate (80 μL, 0.845 mmol) and cesium carbonate (852 mg, 2.61 mmol) in 50 mL of acetone was stirred under nitrogen at room temperature for 19 h (overnight). The acetone was removed under reduced pressure and the residue partitioned between methylene chloride and water. The organic layer was separated and the aqueous layer extracted two times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give methyl ({6-[2-(1-methyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetate (289 mg, 90%) as a tan solid, mp 187-189° C. Elemental Analysis for C25H20N2O4 Calc'd: C, 72.80; H, 4.89; N, 6.79. Found: C, 71.55; H, 4.86; N, 6.53

Workup

  1. customThe acetone was removed under reduced pressure
  2. customthe residue partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted two times with methylene chloride
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-2c9693b886b84824be70b1fc9afa555a
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

Loading…