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Water → 4-(benzyloxy)-2-({[3,5-dichloro-6-(tetrahydro-2H-pyran-4-ylmethoxy)pyridin-2-yl]oxy}methyl)-3-methylquinoline

HRID 384447
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HRID 384447 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([O:10][CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.[CH2:18]([O:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([CH2:36][OH:37])[C:27]=1[CH3:38])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+].O>CN(C=O)C>[CH2:18]([O:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([CH2:36][O:37][C:2]2[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([O:10][CH2:11][CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:3]=2)[C:27]=1[CH3:38])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 595272172,3,5-trichloro-6-(tetrahydro-2H-pyran-4-ylmethoxy)pyridineHCID 68508380[4-(Benzyloxy)-3-methylquinolin-2-yl]methanol

생성물 1

HCID 595269174-(benzyloxy)-2-({[3,5-dichloro-6-(tetrahydro-2H-pyran-4-ylmethoxy)pyridin-2-yl]oxy}methyl)-3-methylquinoline수율 64.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2,3,5-trichloro-6-(tetrahydro-2H-pyran-4-ylmethoxy)pyridine (214 mg) and [4-(benzyloxy)-3-methylquinolin-2-yl]methanol (222 mg) were dissolved in DMF (5 mL), and 60% sodium hydride (40 mg) was added thereto, followed by stirring at room temperature for 3 hours. Water (30 mL) was added to the reaction mixture, followed by extraction with ethyl acetate (80 mL). The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 4-(benzyloxy)-2-({[3,5-dichloro-6-(tetrahydro-2H-pyran-4-ylmethoxy)pyridin-2-yl]oxy}methyl)-3-methylquinoline (250 mg).

후처리

  1. extractionfollowed by extraction with ethyl acetate (80 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-1f14397c2b104fbda80c76fda51bccf4
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367702B2

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