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Picolinic acid → 3-(4-((4,4-Dimethylcyclohex-1-en-1-yl)oxy)phenyl)pyridin-2-amine

HRID 1748061
Notes
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Reaction equation

HRID 1748061 reaction equation
N1C=CC=CC=1C(O)=O.[NH2:10][C:11]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:15][CH:14]=[CH:13][N:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:33]1[CH2:38][CH2:37][C:36]([CH3:40])([CH3:39])[CH2:35][CH:34]=1>[Cu]I.CS(C)=O>[CH3:39][C:36]1([CH3:40])[CH2:37][CH2:38][C:33]([O:23][C:20]2[CH:21]=[CH:22][C:17]([C:16]3[C:11]([NH2:10])=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:18][CH:19]=2)=[CH:34][CH2:35]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 62657Potassium Phosphate, TribasicHCID 467386891-Bromo-4,4-dimethylcyclohexeneHCID 667484774-(2-Aminopyridin-3-yl)phenol

Product 1

HCID 667493853-(4-((4,4-Dimethylcyclohex-1-en-1-yl)oxy)phenyl)pyridin-2-amineYield 71.2%

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

Copper(I) iodide (102 mg) was added to a mixture of picolinic acid (66.1 mg), 4-(2-aminopyridin-3-yl)phenol (500 mg), tripotassium phosphate (1710 mg), 1-bromo-4,4-dimethylcyclohex-1-ene (609 mg) and DMSO (8 mL). The mixture was stirred at 130° C. under nitrogen for 16 hr. The insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc). Silica-gel was added to the filtrate and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane) to give the title compound (563 mg) as an off-white amorphous solid.

Workup

  1. customThe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  2. additionSilica-gel was added to the filtrate
  3. customthe volatiles were removed in vacuo
  4. customwas purified by column chromatography (NH-silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-2928262fad02459e8d2e42d8b9ef96d5
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150591B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes