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

HRID 2174923
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HRID 2174923 반응식
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]Br)[CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:31][CH:28]3[CH2:29][CH2:30][N:25]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:26][CH2:27]3)[N:7]=2)[C:3]=1[CH3:11]
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 441192325-Bromo-4-methyl-1H-indazole

생성물 1

HCID 117690409Tert-butyl 4-[(5-bromo-4-methyl-2H-indazol-2-yl)methyl]piperidin-1-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

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온도
60 °C

실험 절차

5 g of 5-bromo-4-methyl-1H-indazole was dissolved in 110 ml DMF and treated with 11.5 g of caesium carbonate and 7.9 g of N-Boc-4-(bromomethyl)piperidine. The mixture was stirred for 3 hrs at 60° C. and overnight at RT. The reaction mixture was next diluted with ethyl acetate, and the organic phase was washed twice with water, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4 via a 65i-Si column Gradient: hexane/ethyl acetate 0-100%. Yield: 3.53 g of the title compound.

후처리

  1. washthe organic phase was washed twice with water
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified chromatographically on the Biotage SP4 via a 65i-Si column Gradient

출처 및 근거

ORD 기록
ord-0bb6e0007afe46bb9a2880c4863d4095
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062041B2

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