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

HRID 425919Notes

Reaction equation

HRID 425919 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 [(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-d159ef8f183041d1a350e529c5bc68ae
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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