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Trimethylphosphine → 4-[(5-chloropyridin-2-yl)methoxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497376
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인쇄 미리보기

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HRID 1497376 반응식
[CH:1]1([N:4]2[C:12]([CH3:13])=[C:11]3[C:6]([CH:7]=[CH:8][C:9]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])=[CH:10]3)=[N:5]2)[CH2:3][CH2:2]1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29]O)=[N:27][CH:28]=1.CP(C)C>O1CCCC1.C(OCC)(=O)C>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][O:20][C:17]2[CH:18]=[CH:19][N:14]([C:9]3[CH:8]=[CH:7][C:6]4[C:11](=[C:12]([CH3:13])[N:4]([CH:1]5[CH2:2][CH2:3]5)[N:5]=4)[CH:10]=3)[C:15](=[O:21])[CH:16]=2)=[N:27][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 68983TrimethylphosphineHCID 20537893(5-Chloropyridin-2-yl)methanolHCID 1177986831-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 1177986844-[(5-chloropyridin-2-yl)methoxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one수율 50.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (30 mg) in tetrahydrofuran (2 ml) were added (5-chloropyridin-2-yl)methanol (31 mg), bis(2-methoxyethyl)azodicarboxylate (55 mg) and trimethylphosphine (1 M tetrahydrofuran solution, 235 μl) at room temperature, and the mixture was stirred at the same temperature for 2 hr. The mixture was diluted with ethyl acetate, and washed with water, 1 M aqueous sodium hydroxide solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) and recrystallized from ethyl acetate to give the title compound (22 mg).

후처리

  1. washwashed with water, 1 M aqueous sodium hydroxide solution and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  5. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-99b655fc09664f808d82ec396d039ce6
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199963B2

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