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Triethylamine → 1-(5-bromopyridin-2-yl)-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881828
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HRID 1881828 반응식
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([CH:32]=[O:33])=[N:30][CH:31]=1.C(N(CC)CC)C>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([C:32](=[O:33])[CH2:16][CH2:15][C:14](=[O:17])[CH:13]([C:10]2[CH:9]=[CH:8][C:7]([S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[CH:12][CH:11]=2)[CH2:18][CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[N:30][CH:31]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 98775625-Bromopyridine-2-carbaldehydeHCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

생성물 1

HCID 593313481-(5-bromopyridin-2-yl)-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione수율 84.1%

시약·촉매·용매 3

HCID 2833352
3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride
촉매
HCID 702Ethanol용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.00 g) in ethanol (10 mL) were added 5-bromopyridine-2-carbaldehyde (640 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (85 mg) and triethylamine (175 μL), and the mixture was stirred with heating under reflux overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (1.29 g, yield 84%) was obtained as a yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 536 (MH+).

후처리

  1. temperaturewith heating
  2. temperatureunder reflux overnight
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d29bd1429f80428b8387dd1a24e2d4ff
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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