4-Chloro-2-[4-(trifluoromethyl)phenyl]pyridine → 7-[2-(4-Trifluoromethyl-phenyl)-pyridin-4-yloxy]-quinoline

HRID 133678Notes

Reaction equation

HRID 133678 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:3]=1.[OH:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][CH:25]=[N:26]2)=[CH:21][CH:20]=1.CC(C)([O-])C.[K+]>CN1CCCC1=O>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([C:4]2[CH:3]=[C:2]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]=[CH:24][CH:25]=[N:26]4)=[CH:21][CH:20]=3)[CH:7]=[CH:6][N:5]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 218652924-Chloro-2-[4-(trifluoromethyl)phenyl]pyridineHCID 23665647Potassium tert-butoxideHCID 1354268667-Hydroxyquinoline

Product 1

HCID 597357547-[2-(4-Trifluoromethyl-phenyl)-pyridin-4-yloxy]-quinoline

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

This material was prepared following the methods described in Example 8 (b) using 4-chloro-2-(4-trifluoromethyl-phenyl)-pyridine (Example 8 (a), 43 mg, 0.16 mmol), 7-hydroxyquinoline (46 mg, 0.32 mmol) and potassium t-butoxide (38 mg, 0.34 mmol) in N-methylpyrrolidone (0.6 mL). The compound was purified by flash chromatography using 1:4 of EtOAc/hexanes, to provide the title compound as a white solid. MS (ESI, pos. ion) m/z: 367 (M+1).

Workup

  1. customThis material was prepared
  2. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-9fcd5c9b2c87439285e838f1304eed0c
Source dataset
uspto-grants-2008_06
Patent number
US07390907B2

Reaction notes

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