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

HRID 456825Notes

Reaction equation

HRID 456825 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][CH:4]=[C:3]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([OH:23])[CH:17]=[CH:16]2.Br[CH2:25][C:26]#[N:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=[C:3]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([O:23][CH2:25][C:26]#[N:27])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 184390326-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol

Product 1

HCID 18439033{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrileYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described in step 1 of Example 4, the title compound was prepared from 6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.45 g, 1.5 mmol), prepared in the previous step, bromoacetonitrile (0.216 g, 1.8 mmol) and cesium carbonate (2.45 g, 7.52 mmol) with the exception that the reaction was complete after 100 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-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile as an off-white solid (0.494 g, 97%), mp 191.5–192.5° C. Elemental Analysis for C23H18N2O Calc'd: C, 81.63; H, 5.36; N, 8.28. Found: C, 81.06; H, 5.14; N, 8.04.

Workup

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

Sources & evidence

ORD record
ord-2e2bc70424064dffb3e1c70ec1f250f5
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

Loading…