Sodium Carbonate → 4-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol

HRID 1766740Notes

Reaction equation

HRID 1766740 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[C:5]([NH2:8])=[N:6][CH:7]=1.[C:19](=[O:22])([O-])[O-].[Na+].[Na+]>COCCOC.O.C(OCC)(=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:3]2[CH:4]=[CH:5][C:19]([OH:22])=[CH:7][CH:2]=2)=[CH:3][C:4]=1[O:9][CH2:10][C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:18]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 211114873-(2,6-Dichlorobenzyloxy)-5-bromopyridin-2-amine

Product 1

HCID 104286454-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-3-(2,6-dichloro-benzyloxy)-pyridin-2-ylamine (example I(a), 100 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3-2-dioxabordan-2-yl) phenol (86 mg, 0.35 mmol), bis(triphenylphosphine) palladium(II) chloride (8 mg, 0.009 mmol) and sodium carbonate (91 mg, 0.87 mmol) in ethylene glycol dimethyl ether (10 mL) and water (0.5 mL) was heated to reflux under nitrogen for 18 hours. The reaction was cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water, brine, dried over Na2SO4, and purified on silica column to afford 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol as light pine crystals (89 mg, 85% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 18 hours
  3. washThe mixture was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. custompurified on silica column

Sources & evidence

ORD record
ord-8189ddcbb8ef4a73b0e60e47a1d014ee
Source dataset
uspto-grants-2007_06
Patent number
US07230098B2

Reaction notes

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