Cesium carbonate → N,N-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine

HRID 1052255ノート

反応式

HRID 1052255 の反応式
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.Cl.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

生成物 1

HCID 57722832N,N-Dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine収率 88%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (60.0 mg, 0.309 mmol), β-dimethylaminoethyl chloride hydrochloride (49.0 mg, 0.340 mmol) and cesium carbonate (0.302 g, 0.928 mmol) in acetonitrile (1 mL) was stirred at 90° C. overnight. The reaction mixture was cooled to ambient temperature, quenched with water, and extracted with methylene chloride. The combined organic layers were dried over MgSO4, then filtered and concentrated under reduced pressure to give the desired product (60 mg, 88%). LCMS calculated for C13H25BN3O2 (M+H)+: m/z=266.2. Found: 266.2.

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4313058b79b9456d8ee79888b34eed98
出典データセット
uspto-grants-2016_07
特許番号
US09388185B2

反応ノート

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