Tributyltin Chloride → 6-chloro-1-ethyl-3-tributylstannyl-1H-indazole

HRID 246031노트

반응식

HRID 246031 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](I)=[N:7][N:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[CH2:19]([Sn:23]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])Cl)[CH2:20][CH2:21][CH3:22]>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Sn:23]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:19][CH2:20][CH2:21][CH3:22])=[N:7][N:8]2[CH2:11][CH3:12])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 712805146-chloro-1-ethyl-3-iodo-1H-indazoleHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 712796006-chloro-1-ethyl-3-tributylstannyl-1H-indazole수율 58%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 6-chloro-1-ethyl-3-iodo-1H-indazole (150 mg, 0.47 mmol) in THF (3 mL) at 0° C. was slowly added isopropylmagnesium chloride (2.0 M in THF, 0.28 mL, 0.56 mmol). The bright yellow heterogeneous reaction mixture was stirred at 0° C. for 20 min then tributylchlorostannane (0.15 mL, 0.56 mmol) was added dropwise. Stirring was continued at 0° C. for 20 min then at room temperature for 2 h. The reaction mixture was quenched with water and extracted with EtOAc (2×). The combined organics were washed with brine then dried over MgSO4 and concentrated. The exact reaction was repeated once more on the same scale. The residues from the two runs were combined and purified by silica gel chromatography with 10% to 50% EtOAc/heptane (0.5% Et3N) to provide 128 mg (29%) of 6-chloro-1-ethyl-3-tributylstannanyl-1H-indazole as a colorless oil.

후처리

  1. customat 0° C.
  2. stirringStirring
  3. waitwas continued at 0° C. for 20 min
  4. waitat room temperature for 2 h
  5. customThe reaction mixture was quenched with water
  6. extractionextracted with EtOAc (2×)
  7. washThe combined organics were washed with brine
  8. dry with materialthen dried over MgSO4
  9. concentrationconcentrated
  10. customThe exact reaction
  11. custompurified by silica gel chromatography with 10% to 50% EtOAc/heptane (0.5% Et3N)

출처 및 근거

ORD 기록
ord-9ff42a06cf564510a6776b4076a7e674
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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