Sodium hydride → 6-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 245803

반응식

HRID 245803 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178424716-Bromo-1H-indazole

생성물 1

HCID 673619576-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole수율 69%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

In a round-bottomed flask 6-bromo-1H-indazole (0.70 g, 3.55 mmol) was dissolved in DMF (7.5 ml). The reaction mixture was cooled to 0° C. and sodium hydride (60% dispersion in mineral oil, 172 mg, 4.3 mmol) was added). The reaction mixture was warmed to room temperature and stirred for 30 min then cooled back to 0° C. and SEM-Cl (0.76 ml, 4.28 mmol) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was warmed to room temperature. After 1.5 h the reaction was 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 0-10% EtOAc) to give 802 mg (69%) of 6-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole as a light yellow oil.

후처리

  1. temperatureThe reaction mixture was warmed to room temperature
  2. temperaturethen cooled back to 0° C.
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. temperaturethe reaction mixture was warmed to room temperature
  6. customAfter 1.5 h the reaction was quenched with water
  7. extractionextracted with diethyl ether (2×)
  8. washThe combined organic layers were washed twice with water and once with brine
  9. dry with materialthen dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was chromatographed over silica gel with EtOAc/Hexanes (gradient 0-10% EtOAc)

출처 및 근거

ORD 기록
ord-31e08321afa54c9e94d4e7503a8b71a5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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