Allyl iodide → 6-Allyloxy-1H-indazole

HRID 1815936

反応式

HRID 1815936 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH:18]=[CH2:19]>CC(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[CH2:19]([O:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][NH:1]2)=[CH:5][CH:6]=1)[CH:18]=[CH2:17]

参加物

6

反応物 3

HCID 11166Allyl iodide2 回HCID 11430Potassium Carbonate2 回HCID 1354839876-hydroxy-1H-indazole

生成物 1

HCID 224965696-Allyloxy-1H-indazole収率 56.3%

試薬・触媒・溶媒 2

HCID 10796Cesium carbonate触媒HCID 180Acetone溶媒

実験手順

To a solution of 1H-indazol-6-ol (20.0 g, 150 mmol) in acetone (450 mL) was added pulverized potassium carbonate (22.4 g, 162 mmol), cesium carbonate (2.00 g, 5.7 mmol), and allyl iodide (14.63 mL, 160 mmol) and the mixture was stirred for 18 h at ambient temperature. Additional potassium carbonate (5.00 g, 36 mmol) and allyl iodide (1.4 mL, 15 mmol) were added and the mixture was stirred for 2 h followed filtration. Water (200 mL) was added to the filtrate and the volume of the mixture was reduced by about half in vacuo and extracted with dichloromethane (2×100 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by chromatography (silica, 20% to 50% EtOAc/hexane) to give a yellow solid (14.7 g, 56%): mp 110-112° C.; LC/MS (+APCI) m/z 175 (M+H). Unreacted starting material was recovered (4.71 g).

後処理

  1. stirringthe mixture was stirred for 2 h
  2. filtrationfiltration
  3. additionWater (200 mL) was added to the filtrate
  4. extractionextracted with dichloromethane (2×100 mL)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated to a residue which
  7. customwas purified by chromatography (silica, 20% to 50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-dd6fe07f1e8646f1b5c5683ed6a01535
出典データセット
uspto-grants-2005_04
特許番号
US06881749B2

関連ノート

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