Hydrogen Peroxide → 6-(4-Methylthiazol-2-ylamino)-5-phenoxypyridin-3-ol

HRID 1806026Notes

Reaction equation

HRID 1806026 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.[Li]C.C([Li])CCC.C([O:32]B(OC(C)C)OC(C)C)(C)C.[OH-].[Na+].OO>C1COCC1.CO>[CH3:14][C:12]1[N:13]=[C:9]([NH:8][C:5]2[N:6]=[CH:7][C:2]([OH:32])=[CH:3][C:4]=2[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:10][CH:11]=1

Participants

9

Reactant 6

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 21531Triisopropyl borateHCID 247655435-Bromo-N-(4-methylthiazol-2-yl)-3-phenoxypyridin-2-amineHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 247645186-(4-Methylthiazol-2-ylamino)-5-phenoxypyridin-3-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

N-(5-Bromo-3-phenoxypyridin-2-yl)-4-methylthiazol-2-amine (2.66 mmol) is dissolved in THF (30 mL) and cooled to −78° C. MeLi (2.07 mL, 3.32 mmol) is slowly added and the reaction mixture is stirred for 10 minutes. n-Butyllithium (1.33 mL, 3.32 mmol) is added and the reaction mixture is stirred for 15 minutes. Triisopropylborate (0.613 mL, 2.66 mmol) is added and the reaction mixture is stirred for 30 minutes. The reaction mixture is warmed to 0° C., and methanol (5 mL), 10% aqueous NaOH (5.1 mL, 12.8 mmol), and 30% aqueous H2O2 (1.27 mL, 13.3 mmol) are added. The reaction mixture is stirred at 0° C. for 1 hour, then purified by silica gel chromatography (10-20% EtOAc in hexanes) to afford 6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ol.

Workup

  1. stirringthe reaction mixture is stirred for 15 minutes
  2. stirringthe reaction mixture is stirred for 30 minutes
  3. temperatureThe reaction mixture is warmed to 0° C.
  4. stirringThe reaction mixture is stirred at 0° C. for 1 hour
  5. custompurified by silica gel chromatography (10-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5478e0bbfcbf47e3852f0250071fd05f
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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