Cesium carbonate → 1-Benzyl-5-(2-chloro-4-trifluoromethyl-phenoxy)-1h-indole

HRID 854503Notes

Reaction equation

HRID 854503 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:23][C:24]=1F.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C:24]3[CH:23]=[CH:22][C:21]([C:26]([F:29])([F:28])[F:27])=[CH:20][C:19]=3[Cl:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-HCID 107754621H-Indol-5-ol, 1-(phenylmethyl)-

Product 1

HCID 685477281-Benzyl-5-(2-chloro-4-trifluoromethyl-phenoxy)-1h-indoleYield 68.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 0.413 g (1.85 mmol) 1-benzyl-5-hydroxy-1H-indole, 0.3 ml (2.2 mmol) 3-chloro-4-fluorobenzotrifluoride, and 1.0 g (3.0 mmol) Cs2CO3 in 12 ml DMF was heated to 130° C. with stirring for 16 hr. The solution was allowed to cool and then filtered to remove Cs2CO3. The solution was concentrated under vacuum and chromatographed on silica using 5–7% EtOAc-hexane to afford 0.51 g 1-benzyl-5-(2-chloro-4-trifluoromethyl-phenoxy)-1H-indole as an oil.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customto remove Cs2CO3
  4. concentrationThe solution was concentrated under vacuum
  5. customchromatographed on silica using 5–7% EtOAc-hexane

Sources & evidence

ORD record
ord-bd503e38b0494b908ee085b2707f87dc
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

Loading…