Pyridine → HCID 10433187, compound

HRID 1785915Notes

Reaction equation

HRID 1785915 reaction equation
[NH2:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])[C@@H:4]([CH3:21])[CH2:3]1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.N1C=CC=CC=1.[C:38](OCC)(=[O:40])[CH3:39]>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([N:1]([C@H:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:12](=[O:13])[C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[C@@H:4]([CH3:21])[CH2:3]2)[C:38](=[O:40])[CH3:39])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 742994-Chlorophenylboronic acidHCID 68923463HCID 68923463, compound

Product 1

HCID 10433187HCID 10433187, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S,4R)-(4-amino-2-methyl-3,4-dihydro-2H-quinolin-1-yl)-(4-fluoro-phenyl)-methanone (1.0 g, 3.5 mmol) in DMF (20 mL, dry) was added 4-chlorophenylboronic acid (1.1 g, 7.0 mmol), pyridine (850 uL, 10.5 mmol) and copper(II)acetate (1.27 g, 7.0 mmol). The heterogeneous green mixture was stirred open to air for 1 h and then warmed to 60° C. and stirred over night (14 h). The mixture was then cooled to rt, poured into rapidly stirred ethyl acetate (150 mL); solids were removed by filtration through Celite®. The extracts were washed several times with water and then once with brine. The extracts were then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (95% methylene chloride/5% ethyl acetate) to afford the aniline product (250 mg, 18%) as a yellow oil.

Workup

  1. stirringstirred over night (14 h)
  2. temperatureThe mixture was then cooled to rt
  3. customsolids were removed by filtration through Celite®
  4. washThe extracts were washed several times with water
  5. dry with materialThe extracts were then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica gel chromatography (95% methylene chloride/5% ethyl acetate)

Sources & evidence

ORD record
ord-96f5bfdea7b8462ea145cfeac3af6291
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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