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Ammonium Acetate → 5-bromo-2-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine

HRID 1881968
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인쇄 미리보기

반응식

HRID 1881968 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[CH2:9][CH2:10][C:11](=O)[CH:12]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH:29]3[CH2:31][CH2:30]3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)[CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[N:6][CH:7]=1.C([O-])(=O)C.[NH4+:38]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:38][C:11]([CH:12]([C:20]3[CH:21]=[CH:22][C:23]([S:26]([CH:29]4[CH2:31][CH2:30]4)(=[O:27])=[O:28])=[CH:24][CH:25]=3)[CH2:13][CH:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[CH:10][CH:9]=2)=[N:6][CH:7]=1
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참가 물질

5

반응물 2

HCID 517165Ammonium AcetateHCID 593313481-(5-bromopyridin-2-yl)-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

생성물 1

HCID 593312485-bromo-2-(5-[1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine수율 96%

시약·촉매·용매 2

HCID 176Acetic Acid용매
HCID 8857
Ethyl Acetate
용매

반응 조건

온도
110 °C

실험 절차

To a solution (10 mL) of 1-(5-bromopyridin-2-yl)-5-[4-(cyclopropylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (1.29 g) in acetic acid (10 mL) was added ammonium acetate (3.00 g), and the mixture was stirred at 110° C. for 45 min. 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 aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (1.12 g, yield 96%) was obtained as a white amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 517 (MH+).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-71727e4eae344ce4a35d0ac2bda7869f
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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