HCID 18923777, compound → 2-(4-Hydroxyphenyl)-3-(4-methoxyphenyl)-6-(4-fluorophenyl)pyridine

HRID 1379693Notes

Reaction equation

HRID 1379693 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:19][CH:18]=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C1COCC1.CCO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:19][CH:18]=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:16]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 18923777HCID 18923777, compound

Product 1

HCID 1361742502-(4-Hydroxyphenyl)-3-(4-methoxyphenyl)-6-(4-fluorophenyl)pyridineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The 2-(4-benzyloxyphenyl)-3-(4-methoxyphenyl)-6-(4-fluorophenyl)pyridine (1.2 g, 2.6 mmol) was dissolved in 50 mL of THF/ EtOH (1:1), 5% Pd/ C (0.3 g, 0.14 mmol Pd) added, and the reaction mixture hydrogenated at 40 psi for 4 h at rt. The reaction mixture was filtered and concentrated to give 0.86 g (90% yield) of white foam: mp 143°-145° C.; 1H NMR (CDCl3) d 3.83 (s, 3H, OCH3), 4.78 (s, 1H, ArOH), 6.72-6.75 (d, 2H, J=8 Hz, ArH), 6.84-6.87 (d, 2H, J=8 Hz, ArH), 7.14-7.27 (m, 4H, ArH), 7.37-7.40 (d, 2H, J=8 Hz, ArH), 7.69-7.73 (m, 2H, ArH), 8.10-8.15 (m, 2H, ArH); MS(FD) 371(M+). Anal. Calcd for C24H18 NO2F: C, 77.61; H, 4.89; N, 3.77. Found: C, 77.88; H, 5.12; N, 3.51.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0d70ef1a0e6942fab606e5f6f7f93dd2
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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