Water → 3-Iodo-1-methyl-1H-indazol-5-ol

HRID 246615

反応式

HRID 246615 の反応式
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[N:13]=[C:12]2[I:19])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[I:19][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=2)[N:14]([CH3:18])[N:13]=1

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 712798665-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole

生成物 1

HCID 712797213-Iodo-1-methyl-1H-indazol-5-ol収率 120.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-(tert-butyldimethylsilyloxy)-3-iodo-1-methyl-1H-indazole (1 g, 2.57 mmol) in THF (5 mL) was added TBAF (6.42 mL, 12.85 mmol) at 0° C., after the addition, the reaction mixture was warmed to room temperature and stirred for 0.5 hour, then H2O (25 mL) was added to the mixture and product extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure, the residue was triturated with petroleum ether (5 mL), filtered and dried to give 3-iodo-1-methyl-1H-indazol-5-ol (0.85 g, 93.3%) as a white solid. Crude material used into the next step without further purification. LCMS: (M+H)+=275.

後処理

  1. additionafter the addition
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was triturated with petroleum ether (5 mL)
  7. filtrationfiltered
  8. customdried

出典と根拠

ORDレコード
ord-20005cc252234a39a4d30a9279a8817d
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

関連ノート

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