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Potassium Carbonate → 4-(1H-indol-5-yloxy)-5-(3,4-dimethoxyphenyl)nicotinonitrile

HRID 506168
Notes
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Reaction equation

HRID 506168 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1.[OH:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[CH:24]2.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH3:19][O:18][C:12]1[CH:11]=[C:10]([C:3]2[CH:4]=[N:5][CH:6]=[C:7]([C:2]=2[O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH:25]=[CH:24]3)[C:8]#[N:9])[CH:15]=[CH:14][C:13]=1[O:16][CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 160545-HydroxyindoleHCID 251297854-Chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile

Product 1

HCID 445738724-(1H-indol-5-yloxy)-5-(3,4-dimethoxyphenyl)nicotinonitrileYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile (120 mg, 0.44 mmol), 5-hydroxyindole (71 mg, 0.53 mmol) and K2CO3 (91 mg, 0.66 mmol) in CH3CN (4.0 mL) was heated at 80° C. for 4 h. After cooling to r.t., the reaction mixture was diluted with water (20 mL) and the precipitate was collected by filtration and washed with ether containing MeOH to give 121 mg (74%) of 5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-yloxy)nicotinonitrile 220 as a tan solid. MS: 372.2; melting range: 192-194° C.

Workup

  1. temperatureAfter cooling to r.t.
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with ether
  4. additioncontaining MeOH

Sources & evidence

ORD record
ord-43f5c823345840059f0cc37161747be1
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781591B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes