Sodium hydride → 4-((2-Bromopyridin-3-yl)methyl)morpholin-3-one

HRID 1517602노트

반응식

HRID 1517602 반응식
[Br:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][C:13]1=[O:18]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:7]([CH2:8][N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 109010782-Bromo-3-(bromomethyl)pyridine

생성물 1

HCID 582686224-((2-Bromopyridin-3-yl)methyl)morpholin-3-one수율 66%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-bromo-3-bromomethyl-pyridine (0.68 g, 2.36 mmol) in dimethylformamide (10 mL) are added sodium hydride (0.11 g, 60% suspension, 2.82 mmol), morpholin-3-one (0.20 g, 1.97 mmol) and tetrabutylammonium iodide (catalytic) at 0° C. The mixture is stirred at room temperature for 16 hours. After completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL). The aqueous layer is extracted with ethyl acetate (2×25 mL) and the combined organic extracts are dried over sodium sulfate and concentrated in vacuo. The crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45) to yield 0.35 g (66%) of the title compound. MS (m/z): 271/273 (M+1, M+3).

후처리

  1. customAfter completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL)
  2. extractionThe aqueous layer is extracted with ethyl acetate (2×25 mL)
  3. dry with materialthe combined organic extracts are dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45)

출처 및 근거

ORD 기록
ord-eca5ef5598b44329a6130dbd66720b76
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

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