Methyl iodide → 5-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole

HRID 245952

反応式

HRID 245952 の反応式
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[I:16])([CH3:4])([CH3:3])[CH3:2].[CH3:19]C(C)([O-])C.[K+].CI>C1COCC1>[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:19])[N:11]=[C:10]2[I:16])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178455023HCID 178455023、化合物

生成物 1

HCID 712798665-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

In a round-bottomed flask, 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1H-indazole (1.65 g, 4.41 mmol) was dissolved in THF (16 ml). The solution was cooled to 0° C. and potassium tert-butoxide (697 mg, 6.22 mmol) was added. The reaction mixture was stirred at 0° C. for 30 min then methyl iodide (0.38 ml, 6.08 mmol) was added dropwise. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 4.5 h. The reaction was quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-10% EtOAc) to give 770 mg (45%) of 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1-methyl-1H-indazole as a light yellow solid.

後処理

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 4.5 h
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc (2×)
  6. washThe combined organic layers were washed with water and brine
  7. dry with materialthen dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-10% EtOAc)

出典と根拠

ORDレコード
ord-2f4e756a8ff646c388a9d3e5f335b719
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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