Morpholine → 2-Methoxy-3-morpholino-5-nitropyridine

HRID 1620103

반응식

HRID 1620103 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:56]1[C:57]([O:65][CH3:66])=[N:58][CH:59]=[C:60]([N+:62]([O-:64])=[O:63])[CH:61]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:66][O:65][C:57]1[C:56]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:61][C:60]([N+:62]([O-:64])=[O:63])=[CH:59][N:58]=1

참가 물질

8

반응물 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 215844513-Bromo-2-methoxy-5-nitropyridine

생성물 1

HCID 680279252-Methoxy-3-morpholino-5-nitropyridine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Morpholine (54 μl), cesium carbonate (336 mg), Pd2(dba)3 (57 mg), and Xantphos (72 mg) were added to a 1,4-dioxane (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (96 mg) in a nitrogen atmosphere, followed by stirring at 100° C. for 10 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1), and a yellow solid of 2-methoxy-3-morpholino-5-nitropyridine (54 mg) was thus obtained.

후처리

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resultant was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1)

출처 및 근거

ORD 기록
ord-f27689bc3ad54f79a56637174f7502b7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772320B2

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