Cesium carbonate → HCID 68452787, compound

HRID 2355121Notes

Reaction equation

HRID 2355121 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([OH:32])[CH:26]=[CH:25]4)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:34][C:35]#[N:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([O:32][CH2:34][C:35]#[N:36])[CH:26]=[CH:25]4)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 68452504HCID 68452504, compound

Product 1

HCID 68452787HCID 68452787, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-[2-(1-benzyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthol (137 mg, 0.329 mmol), prepared in step 4 of Example 5, bromoacetonitrile (28 μL, 0.402 mmol) and cesium carbonate (213 mg, 0.402 mmol) in 20 mL of acetone was stirred under nitrogen at room temperature for 20 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 ({6-[2-(1-benzyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (142 mg, 95%) as a tan solid, mp 205-208° C. Elemental Analysis for C30H21N3O2+0.38 mole of CH2Cl2 Calc'd: C, 74.86; H, 4.50; N, 8.62. Found: C, 73.58; H, 4.74; N, 8.32.

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-f54e3fa960124c3bb7c3947fd7765f58
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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