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

HRID 57526

반응식

HRID 57526 반응식
[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

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-2910dcc4677c4e7985ca0045b2de53aa
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

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