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1,2-Dibromoethane → HCID 59632449, 화합물

HRID 2369062
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HRID 2369062 반응식
Br[CH2:2][CH2:3]Br.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:16]([C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:23]=3)=[CH:20][CH:21]=2)=[CH:15][C:14]([CH2:32][C:33]#[N:34])=[N:13]1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:16]([C:17]2[S:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:31])(=[O:29])=[O:30])[CH:23]=3)=[CH:20][CH:21]=2)=[CH:15][C:14]([C:32]2([C:33]#[N:34])[CH2:3][CH2:2]2)=[N:13]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 59633179HCID 59633179, 화합물

생성물 1

HCID 59632449HCID 59632449, 화합물수율 82%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매

실험 절차

1,2-dibromoethane (40 μL, 0.46 mmol) was added to a stirred suspension of the [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetonitrile (68 mg, 0.15 mmol), benzyltriethylammonium chloride (20 mg, 0.088 mmol), and 50% aqueous NaOH (2 mL) at 0° C., the resulting mixture was stirred at rt overnight. After diluted with water, the mixture was extracted with ether. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-70% EtOAc/hexanes) to give the title compound as a white solid (59 mg, 82%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.84-7.82 (m, 1H), 7.74-7.71 (m, 1H), 7.58-7.43 (m, 5H), 7.21 (d, 1H), 6.79-6.77 (m, 2H), 3.07 9d, 3H), 1.73-1.68 (m, 4H). MS(ES): 480 [M+H]+.

후처리

  1. extractionthe mixture was extracted with ether
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-70% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-9b1d2b0fe3904cff8200b408e381d2b6
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08703805B2

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