Tributyltin Chloride → 1-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole

HRID 246413노트

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HRID 246413 반응식
I[C:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[N:4]([CH3:11])[N:3]=1.C([Mg]Cl)(C)C.[CH2:17]([Sn:21]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])Cl)[CH2:18][CH2:19][CH3:20]>C1COCC1>[CH3:11][N:4]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[C:2]([Sn:21]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:17][CH2:18][CH2:19][CH3:20])=[N:3]1

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 712802793-iodo-1-methyl-4,5,6,7-tetrahydro-1H-indazoleHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 712804701-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-16 °C

실험 절차

In a 25 mL round-bottomed flask, 3-iodo-1-methyl-4,5,6,7-tetrahydro-1H-indazole (62 mg, 237 μmol) was dissolved in THF (3 mL). The colorless solution was cooled to −16° C. (NaCl/ice bath) and isopropylmagnesium chloride 2 M in THF (132 μL, 265 μmol) was added dropwise at −16° C. The reaction mixture was stirred at −16° C. for 20 min. Then, tributylchlorostannane (88.6 mg, 73.8 μL, 272 μmol) was added slowly. The reaction mixture was warmed to 25° C. and stirred for 1.5 h. The reaction mixture was quenched with saturated ammonium chloride solution, extracted with dichloromethane (3×30 mL), organics dried over MgSO4 and concentrated to an off-white waxy solid. The residue was dried under high vacuum yielding 1-methyl-3-(tributylstannyl)-4,5,6,7-tetrahydro-1H-indazole assumed quantitative and taken into next step without further treatment.

후처리

  1. additionwas added dropwise at −16° C
  2. temperatureThe reaction mixture was warmed to 25° C.
  3. stirringstirred for 1.5 h
  4. customThe reaction mixture was quenched with saturated ammonium chloride solution
  5. extractionextracted with dichloromethane (3×30 mL)
  6. dry with materialorganics dried over MgSO4
  7. concentrationconcentrated to an off-white waxy solid
  8. customThe residue was dried under high vacuum

출처 및 근거

ORD 기록
ord-9c95be95defe4c50b4fc0b81e48d6d6e
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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