Sodium hydride → 4-((2-Bromopyridin-3-yl)methyl)morpholin-3-one
Reaction equation
[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]=1Participants
Procedure
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).
Workup
- customAfter completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL)
- extractionThe aqueous layer is extracted with ethyl acetate (2×25 mL)
- dry with materialthe combined organic extracts are dried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45)
Sources & evidence
- ORD record
- ord-eca5ef5598b44329a6130dbd66720b76
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232289B2
Reaction notes
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