Pyridine → (R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one

HRID 1617783노트

반응식

HRID 1617783 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Br:33]Br.C(OCC)(=O)C>CN(C=O)C>[Br:33][C:14]1[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=[C:12]([C:10](=[O:11])[CH2:9][C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH:13]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24408BromineHCID 66668696(R)-5-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one

생성물 1

HCID 67015677(R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (R)-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one (0.1 g, example 223) in DMF (1 mL) were added pyridine (217 μL) and then bromine (12.6 μL) dropwise. The resulting solution was stirred at rt for 2.25 h. The reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted with 2× ethyl acetate. The organic layers were washed with water and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by chromatography (SiO2, n-heptane/ethyl acetate 100:0 to 50:50) to give the title compound as a light brown solid (0.093 g; 78%), MS (ESI+): m/z=489.0 [M+H]+.

후처리

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 2× ethyl acetate
  3. washThe organic layers were washed with water and once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by chromatography (SiO2, n-heptane/ethyl acetate 100:0 to 50:50)

출처 및 근거

ORD 기록
ord-a3d83545c27243abb2aff2bc3f223148
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765730B2

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