Pyridine → 5-(2-fluorophenyl)-1-(4-fluorophenyl)-2(1H)-quinolinone

HRID 1987033Notes

Reaction equation

HRID 1987033 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C([N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])C.N1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F:24]OB(C1C=CC=CC=1)O.[CH2:34]1CC[CH2:37][CH2:36][CH2:35]1.C([O:43][CH2:44][CH3:45])(=O)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:21]1[CH:22]=[CH:23][CH:17]=[C:16]2[C:20]=1[CH:19]=[CH:45][C:44](=[O:43])[N:13]2[C:14]1[CH:15]=[CH:37][C:36]([F:24])=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 21867204Cyclohexane ethylacetateHCID 66616553Fluorophenylboronic acid

Product 1

HCID 104269275-(2-fluorophenyl)-1-(4-fluorophenyl)-2(1H)-quinolinoneYield 76%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the compound of Example 18(d) (0.1 g, 4.18 mmol), 4-fluorophenylboronic acid (0.118 g, 0.836 mmol), triethylamine (0.116 mL, 0.836 mmol), pyridine (0.068 mL, 0.836 mmol), copper (II) acetate (0.156 g, 0.836 mmol) and powdered 4 Å sieves in dichloromethane (10 mL) was stirred at RT for 7 h. Further quantities of fluorophenylboronic acid (0.06 g), copper (II) acetate (0.075 g) and powdered 4 Å sieves were added and stirring continued for 18 h. The mixture was retreated as above and stirred for a further 5 h then diluted with dichloromethane (20 mL) and filtered through a pad of celite. The filtrate was washed with saturated sodium carbonate and water, dried (Na2SO4) and evaporated in vacuo to give a brown solid. Flash chromatography (silica gel, 1:1 cyclohexane/ethyl acetate) afforded the title compound as a pale brown solid (0.106 g, 76%). MS(EI) m/e 334 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.65 (d of d, J=10 and 5 Hz, 1H), 7.5-7.2 (m, 9H), 7.18 (d, J=8 Hz, 1H), 6.73 (d, J=10 Hz, 1H), 6.71 (d, J=10 Hz, 1H).

Workup

  1. stirringstirring
  2. waitcontinued for 18 h
  3. stirringstirred for a further 5 h
  4. filtrationfiltered through a pad of celite
  5. washThe filtrate was washed with saturated sodium carbonate and water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a brown solid

Sources & evidence

ORD record
ord-964a765d4a5844e0a04d402193180eb6
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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