Cesium carbonate → {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile

HRID 456822Notes

Reaction equation

HRID 456822 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([OH:29])[CH:23]=[CH:22]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][C:32]#[N:33].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([O:29][CH2:31][C:32]#[N:33])[CH:23]=[CH:22]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 184390296-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol

Product 1

HCID 18439031{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrileYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described in step 1 of Example 3, the title compound was prepared from 6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.250 g, 0.665 mmol), prepared in step 2 of Example 2, bromoacetonitrile (0.096 g, 0.80 mmol) and cesium carbonate (1.08 g, 3.33 mmol) with the exception that the reaction was complete after 70 minutes at ambient temperature. The crude material was dissolved in methylene chloride and filtered through silica gel (45 g, 200–300 mesh). The solvent was removed under reduced pressure to give {[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile as a beige solid (0.276 g, 100%), mp 156–157° C. Elemental Analysis for C29H22N2O Calc'd: C, 84.03; H, 5.35; N, 6.76. Found: C, 83.15; H, 5.46; N, 6.54.

Workup

  1. filtrationfiltered through silica gel (45 g, 200–300 mesh)
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a1531c2ef4604de1af185df441b37b58
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

Loading…