Cesium carbonate → 4-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole

HRID 219279

反応式

HRID 219279 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[I:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.Br[CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1>CN(C=O)C.O>[I:7][C:8]1[CH:9]=[N:10][N:11]([CH2:14][CH2:15][O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH:12]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 770224-IodopyrazoleHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

生成物 1

HCID 593418524-Iodo-1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of cesium carbonate (20.7 g, 63.4 mmol) and 4-iodopyrazole (10.00 g, 51.6 mmol) in DMF (100 mL) was allowed to stir for 10 min. To the mixture was added 2-(2-bromoethoxy)tetrahydro-2 h-pyran (9.98 ml, 63.4 mmol) and heated at 80° C. overnight. The mixture was diluted with water and extracted with EtOAc (3×50 mL), and subsequently washed with water (2×50 mL) and brine, dried over sodium sulfate, and filtered. The crude mixture was evaporated onto silica gel and purified via MPLC (0% to 50%; EtOAc in hexanes). Isolated 4-iodo-1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazole (15.3 g, 92%) as a clear oil. MS m/z=323.0 [M+1]+. Calc'd for C10H15IN2: 322.1.

後処理

  1. extractionextracted with EtOAc (3×50 mL)
  2. washsubsequently washed with water (2×50 mL) and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe crude mixture was evaporated onto silica gel
  6. custompurified via MPLC (0% to 50%; EtOAc in hexanes)

出典と根拠

ORDレコード
ord-365fe3387d6147119dfb076b00a62b61
出典データセット
uspto-grants-2012_06
特許番号
US08198448B2

関連ノート

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