HCID 21081542、化合物 → HCID 21081507、化合物

HRID 347582

反応式

HRID 347582 の反応式
[H-].[Al+3].[H-].[H-].[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:13][CH2:14][C:15]([C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][C:24]=2[O:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][C:28]=2[F:36])[NH:19][CH:18]=1)=[O:16])=O>COCCOC>[NH2:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24]2[CH:23]=[CH:22][N:21]=[C:20]3[NH:19][CH:18]=[C:17]([CH:15]([OH:16])[CH2:14][OH:13])[C:25]=23)=[C:28]([F:36])[CH:29]=1

参加物

5

反応物 3

HCID 21081542HCID 21081542、化合物HCID 21226445Aluminium lithium hydrideHCID 21584524Aluminiumhydride

生成物 1

HCID 21081507HCID 21081507、化合物収率 45%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To a suspension of anhydrous aluminum hydride (266 mg, 2.0 mmol, Alfa Aesar) in 5 mL of 1,2 dimethoxyethane at 0° C. was added lithium aluminum hydride (1 M soln. in THF, 1.0 mL, 1.0 mmol). A solution of 2-(4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-oxoethyl formate (72 mg, 0.2 mmol) in 5 mL of 1,2-dimethoxyethane was added dropwise. The reaction mixture was stirred at rt for 2 h and quenched by the addition of 5 mL of cold water. The mixture was extracted with EtOAc (3×30 mL) and the combined organic extracts were dried (MgSO4), concentrated in vacuo and purified by flash column chromatography (ISCO RediSep® silica gel cartridge, etuting with 2–10% MeOH in dichloromethane) to give 1-(4-(4-amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethane-1,2-diol (27 mg, 45%): MS(ESI+) m/z 304.3 (M+H)+ and 2-(4-(4-amino-2-fluorophenoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanol (10 mg, 18%): MS(ESI+) m/z 288.3 (M+H)+.

後処理

  1. customquenched by the addition of 5 mL of cold water
  2. extractionThe mixture was extracted with EtOAc (3×30 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by flash column chromatography (ISCO RediSep® silica gel cartridge, etuting with 2–10% MeOH in dichloromethane)

出典と根拠

ORDレコード
ord-046df411627148838070455c804c2027
出典データセット
uspto-grants-2007_02
特許番号
US07173031B2

関連ノート

読み込み中…