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

HRID 911780노트

반응식

HRID 911780 반응식
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

참가 물질

9

반응물 6

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d856fadf935d4c78a75a13a0d7fe9530
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022223B2

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