Sodium hydride → 1-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester

HRID 57526

反応式

HRID 57526 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.Br[CH2:16][CH2:17][O:18][CH3:19].[H-].[Na+]>C1COCC1>[CH3:19][O:18][CH2:17][CH2:16][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 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

生成物 1

HCID 112304911-(2-Methoxyethyl)-1H-pyrazole-4-boronic acid, pinacol ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (200 mg, 1.03 mmol), 1-bromo-2-methoxyethane (280 mg, 2.01 mmol), and NaH (200 mg, 4 mmol) in THF (15 mL) was stirred at reflux for 24 hours, cooled to the ambient temperature, and concentrated in vacuo. The residue was treated with HCl(aq) and extracted with EtOAc. The insoluble solid was removed by filtration, and the organic solution was concentrated to give the title compound. MS (m/z): 253 (M+H)+.

後処理

  1. temperatureat reflux for 24 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with HCl(aq)
  4. extractionextracted with EtOAc
  5. customThe insoluble solid was removed by filtration
  6. concentrationthe organic solution was concentrated

出典と根拠

ORDレコード
ord-2910dcc4677c4e7985ca0045b2de53aa
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

関連ノート

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