8-Hydroxyquinoline → 8-[4-[4-(Trifluoromethyl)phenyl]-2-pyridyloxy]quinoline

HRID 2105624Notes

Reaction equation

HRID 2105624 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[OH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2.[H-].[Na+]>CN(C=O)C.[Cu]I>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([O:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)[CH:7]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 19238-HydroxyquinolineHCID 24758Sodium hydrideHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

Product 1

HCID 578082328-[4-[4-(Trifluoromethyl)phenyl]-2-pyridyloxy]quinoline

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

This material was prepared according to the method described in Example 413 using 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (Example 410 (c), 0.16 g, 0.6 mmol), 8-hydroxyquinoline (0.1 g, 0.7 mmol), sodium hydride (38 mg, 1.0 mmol) and copper (I) iodide (12 mg, 0.06 mmol) in DMF (3 ML). Purification on a Biotage 40S column (3:1 hexanes: EtOAc), provided the title compound as a white solid. MS (ESI, pos. ion) nm/z: 367 (M+1). Anal. Calcd for C21H13F3N2O: C, 68.85; H, 3.58; N, 7.65. Found: C, 68.88; H, 3.59; N, 7.51.

Workup

  1. customThis material was prepared
  2. customPurification on a Biotage 40S column (3:1 hexanes: EtOAc)

Sources & evidence

ORD record
ord-b0a790a9da46403693300f759dba3b44
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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