Tributyltin Chloride → 6-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole

HRID 246027노트

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HRID 246027 반응식
[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([C:9](I)=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:21]([Sn:25]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])Cl)[CH2:22][CH2:23][CH3:24]>C1COCC1>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([Sn:25]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH3:24])=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 712799536-(tert-Butyl)-3-iodo-1-methyl-1H-indazoleHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 712801066-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 6-tert-butyl-3-iodo-1-methyl-1H-indazole (150 mg, 0.45 mmol) in THF (3 mL) at 0° C. was slowly added isopropylmagnesium chloride (2.0 M in THF, 0.27 mL, 0.54 mmol). The bright yellow heterogeneous reaction mixture was stirred at 0° C. for 1 h then tributylchlorostannane (0.15 mL, 0.54 mmol) was added dropwise. Stirring was continued at 0° C. for 20 min then at room temperature for 3 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 to afford 6-tert-butyl-1-methyl-3-tributylstannanyl-1H-indazole as a viscous yellow oil which was used in the next step without further purification.

후처리

  1. customat 0° C.
  2. stirringStirring
  3. waitwas continued at 0° C. for 20 min
  4. waitat room temperature for 3 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

출처 및 근거

ORD 기록
ord-1c673ba749194d31b97dcc6cd2cd285d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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