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Water → Tert-butyl 4-[(5-bromo-6-methyl-2H-indazol-2-yl)methyl]piperidin-1-carboxylate

HRID 2174926
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HRID 2174926 반응식
[Br:1][C:2]1[C:3](C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.S(O[CH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)(C1C=CC(C)=CC=1)(=O)=O.[C:37](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Br:1][C:2]1[C:10]([CH3:37])=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:23][CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH2:28][CH2:29]3)[N:7]=2)[CH:3]=1
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참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineHCID 441192325-Bromo-4-methyl-1H-indazole

생성물 1

HCID 117690376Tert-butyl 4-[(5-bromo-6-methyl-2H-indazol-2-yl)methyl]piperidin-1-carboxylate

시약·촉매·용매 3

HCID 67553
Tetrabutylammonium Iodide
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

10.0 g (47.4 mmol) of 5-bromo-4-methyl-1H-indazole and 21.0 g (56.9 mmol) of tert-butyl 4-[(tosyloxy)methyl]piperidin-1-carboxylate were dissolved in 726 ml DMF. To this were added 21.0 g (56.9 mmol) of tetrabutylammonium iodide and 18.5 g (56.9 mmol) of caesium carbonate and the reaction mixture was heated under nitrogen at 80° C. for 1.5 hrs. For the work-up, it was treated with water and ethyl acetate, the organic phase separated and the aqueous phase extracted several times with ethyl acetate. The organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. After purification by column chromatography, this yielded the title compound in 5 g yield.

후처리

  1. customthe organic phase separated
  2. extractionthe aqueous phase extracted several times with ethyl acetate
  3. washThe organic phases were washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customAfter purification by column chromatography

출처 및 근거

ORD 기록
ord-b0c8f199fd904bceab310c44362716d5
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062041B2

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