Water → 4-[(4-bromo-1,3-thiazol-2-yl)methoxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497390노트

반응식

HRID 1497390 반응식
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[CH:6][C:7]([N:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]3=[O:19])=[CH:8]2)=[N:3]1.[Br:20][C:21]1[N:22]=[C:23]([CH2:26]O)[S:24][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Br:20][C:21]1[N:22]=[C:23]([CH2:26][O:18][C:15]2[CH:16]=[CH:17][N:12]([C:7]3[CH:6]=[CH:5][C:4]4[C:9](=[C:10]([CH3:11])[N:2]([CH3:1])[N:3]=4)[CH:8]=3)[C:13](=[O:19])[CH:14]=2)[S:24][CH:25]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 11041630(4-Bromo-1,3-thiazol-2-yl)methanolHCID 1177986701-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 1178168074-[(4-bromo-1,3-thiazol-2-yl)methoxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one수율 53.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 1-(2,3-dimethyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (50 mg), (4-bromo-1,3-thiazol-2-yl)methanol (76 mg) and triphenylphosphine (154 mg) in tetrahydrofuran (6 ml) was added bis(2-methoxyethyl)azodicarboxylate (138 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) and recrystallized from ethanol-hexane to give the title compound (45 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)
  6. customrecrystallized from ethanol-hexane

출처 및 근거

ORD 기록
ord-8d79f03ca22c418086b335053a62dfb3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199963B2

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