Potassium Iodide → N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamine

HRID 886060

반응식

HRID 886060 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.[H-].[Na+].Br[CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].[I-].[K+]>O1CCCC1.C(OCC)(=O)C.O>[CH2:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH2:22][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)[CH3:18]

참가 물질

8

반응물 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 706082-Bromo-N,N-diethylethanamineHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

생성물 1

HCID 58204670N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamine수율 90%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4,4,5,5-tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (250 mg, 1.29 mmol) and sodium hydride (61.8 mg, 2.58 mmol) in tetrahydrofuran at 0° C. was added 2-bromo-N,N-diethylethanamine (558 mg, 2.58 mmol). The reaction was allowed to warm up to room temperature and was monitored by LCMS. After 90 minutes there was still no reaction and potassium iodide (1.71 g, 10.3 mmol) was added and the reaction was heated at 50° C. overnight. The reaction mixture was diluted with a large volume of ethyl acetate and water and partitioned. The organic layer containing the product was washed with brine and concentrated in vacuo to give clear thick oil confirmed by LCMS to be 100% pure N,N-diethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanamine (340 mg, yield 90%, M+1 294.2)

후처리

  1. additionwas added
  2. temperaturethe reaction was heated at 50° C. overnight
  3. custompartitioned
  4. additionThe organic layer containing the product
  5. washwas washed with brine
  6. concentrationconcentrated in vacuo
  7. customto give clear thick oil

출처 및 근거

ORD 기록
ord-105e0c6c958e4c40b771dbb9d34b5218
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242104B2

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