Cesium carbonate → HCID 68452467, compound

HRID 2355137Notes

Reaction equation

HRID 2355137 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[O:16][C:15]([C:17]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[O:19][C:18]=4[CH2:26][CH2:27][CH2:28][CH3:29])=[N:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:30].Br[CH2:32][C:33]#[N:34].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[O:16][C:15]([C:17]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[O:19][C:18]=4[CH2:26][CH2:27][CH2:28][CH3:29])=[N:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:30][CH2:32][C:33]#[N:34]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 68453973HCID 68453973, compound

Product 1

HCID 68452467HCID 68452467, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-bromo-6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthol (89 mg 0.192 mmol), prepared in the previous step, bromoacetonitrile (16 μL, 0.23 mmol) and cesium carbonate (127 mg, 0.389 mmol) in 20 mL of acetone was stirred under nitrogen at room temperature for 15 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 ({1-bromo-6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (95 mg, 91%) as a brown solid, mp 144-146° C. Elemental Analysis for C27H21BrN2O3 Calc'd: C, 64.68; H, 4.22; N, 5.59. Found: C, 63.90; H, 4.10; N, 5.18.

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-dc068d28186d429595e7e0cfc97c724e
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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