Phenol → HCID 23115993, compound

HRID 1666553Notes

Reaction equation

HRID 1666553 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:10]([CH2:13]C)CC)C.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2C=[CH:33][C:32](Br)=[CH:31][N:30]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[C]=O.C(=O)(O)[O-:39].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([O:28][C:29]2[N:30]=[CH:31][C:32]([C:33]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:39])=[CH:13][N:10]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:16])([CH3:17])[CH3:18]

Participants

9

Reactant 5

HCID 996PhenolHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 21914479tert-Butyl 4-((5-bromopyridin-2-yl)oxy)piperidine-1-carboxylateHCID 178418416HCID 178418416, compound

Product 1

HCID 23115993HCID 23115993, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

Palladium acetate (35 mg, 0.31 mmol), bis(diphenylphosphino)ferrocene (170 mg, 1.54 mmol), phenol (1.5 ml, 17.1 mmol), triethylamine (0.5 ml, 3.6 mmol) were added in that order to a toluene solution (1.0 ml) of 2-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-bromopyridine (550 mg, 1.54 mmol), and stirred in a carbon monoxide atmosphere under normal pressure at 100° C. for 14 hours. The reaction mixture was cooled to room temperature, an aqueous saturated sodium bicarbonate solution was added thereto and extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (C-200, hexane:ethyl acetate=7:3) to obtain the entitled compound (589 mg, 96%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (C-200, hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-04f3f60356fd4e0f8fec43bf310cc404
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

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