Imidazole → 5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

HRID 245950

反応式

HRID 245950 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C>[C:12]([Si:15]([CH3:17])([CH3:16])[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2)([CH3:14])([CH3:13])[CH3:11]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1014381H-Indazol-5-ol

生成物 1

HCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole収率 93.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a round-bottomed flask, 5-hydroxy-1H-indazole (700 mg, 5.22 mmol) was dissolved in DMF (15 ml) and TBDMS-Cl (865 mg, 5.74 mmol) and imidazole (426 mg, 6.26 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to afford 1.21 g (93%) of 5-(tert-butyl-dimethyl-silanyloxy)-1H-indazole as an off-white solid.

後処理

  1. customthen quenched with water
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed twice with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc)

出典と根拠

ORDレコード
ord-9f54cd4bb5d744ff8e1f5e4078908aa2
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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