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Hydrochloric Acid → Methyl 4-(pyridin-4-yl)-1-naphthoate

HRID 352359
Notes
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Reaction equation

HRID 352359 reaction equation
C[Sn](C)(C)[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1.Br[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.Cl>[OH-].[K+].[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:23]1[CH:24]=[CH:25][C:20]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=2)=[CH:21][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 142684-BromopyridineHCID 22711864Methyl 4-(trimethylstannyl)-1-naphthoate

Product 1

HCID 22711890Methyl 4-(pyridin-4-yl)-1-naphthoateYield 60%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 14797Potassium HydroxideSolvent

Procedure

A stirred solution of D7 (9.06 g, 26 mmole) in dry degassed DMF (150 ml) was treated with copper (I) iodide (495 mg, 2.6 mmole), dichlorobis(triphenylphosphine)palladium(II) (1.52 g, 2.2 mmole) and 4-bromopyridine (prepared by suspending the HCl salt (6.07 g, 31 mmole) in 40% KOH solution, extracting with toluene and adding the dried toluene solution to the reaction). The mixture was heated at reflux under argon for 5 h and allowed to cool before removing the DMF under vacuum. The residue was partitioned between EtOAc and 10% NaHCO3 solution and the organics dried (Na2SO4) and chromatographed on silica gel eluting with EtOAc to afford the title compound as a white solid (4.1 g, 60%).

Workup

  1. customdegassed DMF (150 ml)
  2. customprepared
  3. extractionextracting with toluene
  4. additionadding the dried toluene solution
  5. customto the reaction)
  6. temperatureThe mixture was heated
  7. temperatureat reflux under argon for 5 h
  8. temperatureto cool
  9. custombefore removing the DMF under vacuum
  10. customThe residue was partitioned between EtOAc and 10% NaHCO3 solution
  11. dry with materialthe organics dried (Na2SO4)
  12. customchromatographed on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-f90e065b1e2f47e6bcc6fe1072b8b292
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747030B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes