Triethylamine → 3-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridine

HRID 640503노트

반응식

HRID 640503 반응식
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](Cl)=[N:25][OH:26])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>O1CCCC1>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]2[CH:2]=[C:1]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)[O:26][N:25]=2)=[CH:19][CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1860033-EthynylpyridineHCID 722628734-Benzyloxy-phenyl-acetohydroximoyl chloride

생성물 1

HCID 498501823-(3-(4-Benzyloxy-benzyl)-isoxazol-5-yl)-pyridine수율 48.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a tetrahydrofuran (3 mL) solution of 3-ethynylpyridine (50 mg, 0.485 mmol) and (4-benzyloxy-phenyl)-acetohydroximoyl chloride (214 mg, 0.776 mmol) described in Manufacturing Example 1-1-3 was added triethylamine (270 μL, 1.94 mmol), which was stirred for 2.5 hours at room temperature. This mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2) to obtain the title compound (80 mg, 48%).

후처리

  1. customThis mixture was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2)

출처 및 근거

ORD 기록
ord-eaa6b4a38c0944ea91ee82cbc60f31a6
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691882B2

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