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

HRID 245952

반응식

HRID 245952 반응식
[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]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178455023HCID 178455023, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2f4e756a8ff646c388a9d3e5f335b719
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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