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Potassium Carbonate → Tert-butyl 4-(4-bromo-3-cyanopyrazol-1-yl)piperidine-1-carboxylate

HRID 908472
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HRID 908472 반응식
[Br:1][C:2]1[CH:6]=[N:5][NH:4][C:3]=1[C:7]#[N:8].C(=O)([O-])[O-].[K+].[K+].CS(O[CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)(=O)=O>C(#N)C>[Br:1][C:2]1[C:3]([C:7]#[N:8])=[N:4][N:5]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[CH:6]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27356234-Bromo-1H-pyrazole-3-carbonitrileHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

생성물 1

HCID 67388412Tert-butyl 4-(4-bromo-3-cyanopyrazol-1-yl)piperidine-1-carboxylate수율 60.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

4-bromo-2H-pyrazole-3-carbonitrile (500 mg), potassium carbonate (522 mg) and tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate (975 mg) in acetonitrile (15 ml) were stirred at 90° C. overnight. The mixture was concentrated and the residue was dissolved in ethylacetate, washed with water and brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford. tert-butyl 4-(4-bromo-3-cyano-pyrazol-1-yl)piperidine-1-carboxylate (627 mg) The product gave the following characterizing data: NMR Spectrum: (DMSOd6) 1.41 (s, 9H), 1.74 (dd, 1H), 1.78 (dd, 1H), 1.98-2.08 (m, 2H), 2.90 (bs, 2H), 3.95-4.11 (m, 2H), 4.46-4.57 (m, 1H), 8.45 (s, 1H).

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethylacetate
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether
  7. customThe solvent was evaporated to dryness
  8. customto afford

출처 및 근거

ORD 기록
ord-c8043cb860c0442d9b1a214fd3838fb4
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017611B2

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