3-Methoxyphenol → 2-(3-Methoxy-phenoxy)-4-(4-trifluoromethyl-phenyl)-pyridine

HRID 730316

Reaction equation

HRID 730316 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.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.[H-].[Na+]>CN(C=O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][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

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 24758Sodium hydrideHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

Product 1

HCID 578080442-(3-Methoxy-phenoxy)-4-(4-trifluoromethyl-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This material was prepared according to the method described in Example 2 (d) using 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (Example 410 (c), 129 mg, 0.5 mmol), 3-methoxyphenol (66 uL, 0.6 mmol), and sodium hydride (24 mg, 0.6 mmol) in DMF (1 mL). Purification on a Biotage 40S column (8:1 hexanes:EtOAc), provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 346 (M+1). Mp: 77.5-79.6° C.

Workup

  1. customThis material was prepared
  2. customPurification on a Biotage 40S column (8:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-485b61973d254b9d8b8b3f2f9ffb1712
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Linked notes

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