Potassium Carbonate → 4-(3-Cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzaldehyde

HRID 1007490Notes

Reaction equation

HRID 1007490 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].[F:24][C:25]([F:40])([F:39])[C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([C:35]([F:38])([F:37])[F:36])[C:33]=1Cl)[CH:29]=[O:30]>CS(C)=O>[CH:12]1([CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:33]4[C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][C:26]=4[C:25]([F:24])([F:39])[F:40])[CH:3]=3)[NH:7][CH:6]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 226696144-Chloro-3,5-bis(trifluoromethyl)benzaldehydeHCID 226698395-Hydroxy-3-cyclohexylmethyl-indole

Product 1

HCID 226699334-(3-Cyclohexylmethyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Analogously to the procedure of Example V, 2.0 g (8.72 mmol) of 5-hydroxy-3-cyclohexylmethyl-indole are dissolved in 50 ml of DMSO, 1.33 g (9.59 mmol) of potassium carbonate are added, the mixture is stirred for 10 min at room temperature and afterwards 2.41 g (8.72 mmol) of 3,5-bis-trifluoromethyl-4-chlorobenzaldehyde are introduced in portions. After stirring overnight at 50° C., the batch is worked up analogously to Example V and the crude product is chromatographed on silica gel 60 by means of toluene.

Workup

  1. stirringAfter stirring overnight at 50° C.
  2. customthe crude product is chromatographed on silica gel 60 by means of toluene

Sources & evidence

ORD record
ord-54172418369047e28e264876106def35
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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