Tributyltin Chloride → 1-Methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile

HRID 246596노트

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HRID 246596 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[N:4]([CH3:13])[N:3]=1.IC1C2C(=CC(C#N)=CC=2)NN1C.C([Mg]Cl)(C)C.Cl[Sn:33]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH2:36][CH3:37]>C1COCC1>[CH3:13][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[CH:6]=2)[C:2]([Sn:33]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:34][CH2:35][CH2:36][CH3:37])=[N:3]1

참가 물질

6

반응물 4

HCID 15096Tributyltin ChlorideHCID 712794383-Iodo-1-methyl-1H-indazole-6-carbonitrileHCID 866779973-iodo-2-methyl-1H-indazole-6-carbonitrileHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 712798431-Methyl-3-(tributylstannyl)-1H-indazole-6-carbonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-40 °C

실험 절차

The crude mixture of 3-iodo-1-methyl-1H-indazole-6-carbonitrile and 3-iodo-2-methyl-1H-indazole-6-carbonitrile (97 mg, crude) was dissolved in THF (4 mL). The solution was cooled to −40° C. Isopropylmagnesium chloride (0.21 mL, 0.41 mmol, 2M in THF) was added drop-wise at −40° C. The reaction mixture was stirred at −40° C. for 20 min. Then chlorotributyltin (0.11 mL) was added slowly. The reaction mixture was allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was quenched with saturated NH4Cl solution and then extracted with EtOAc (3×5 mL), organics were washed with water (10 mL), brine (2×10 mL) and dried over Na2SO4 and concentrated. The residue was used to the next step without further purification.

후처리

  1. temperatureto warm to room temperature
  2. stirringstirred for 1.5 h
  3. customThe reaction mixture was quenched with saturated NH4Cl solution
  4. extractionextracted with EtOAc (3×5 mL)
  5. washorganics were washed with water (10 mL), brine (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was used to the next step without further purification

출처 및 근거

ORD 기록
ord-c12b5c5f33cf4777a126859380a054a3
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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