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

HRID 908472
ノート
印刷プレビュー

反応式

HRID 908472 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c8043cb860c0442d9b1a214fd3838fb4
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017611B2

反応ノート

読み込み中…

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