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

HRID 911780ノート

反応式

HRID 911780 の反応式
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

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d856fadf935d4c78a75a13a0d7fe9530
出典データセット
uspto-grants-2011_09
特許番号
US08022223B2

反応ノート

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