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

HRID 2174926
ノート
印刷プレビュー

反応式

HRID 2174926 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 67553
Tetrabutylammonium Iodide
触媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b0c8f199fd904bceab310c44362716d5
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062041B2

反応ノート

読み込み中…

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