N-bromobutanimide → 3-methyl-3-(pyrimidin-5-ylmethyl)-5-bromo-1,3-dihydro-2H-indol-2-one

HRID 2389391노트

반응식

HRID 2389391 반응식
[CH3:1][C:2]1([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].[Br:19]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1([CH2:12][C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Br:19])[CH:9]=2)[NH:4][C:3]1=[O:11]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 594437543-methyl-3-(pyrimidin-5-ylmethyl)-1,3-dihydro-2H-indol-2-one

생성물 1

HCID 252556843-methyl-3-(pyrimidin-5-ylmethyl)-5-bromo-1,3-dihydro-2H-indol-2-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

3-Methyl-3-(pyrimidin-5-ylmethyl)-1,3-dihydro-2H-indol-2-one (900 mg, 3.76 mmol) and N-bromosuccinimide (669 mg, 3.76 mmol) in N,N-dimethylformamide (20 mL) were stirred at room temperature for 3 days. The mixture was diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC on Chiralpak AS, eluting with 25% isopropyl alcohol/CO2, to afford the enantiomers of 3-methyl-3-(pyrimidin-5-ylmethyl)-5-bromo-1,3-dihydro-2H-indol-2-one. Enantiomer A was isolated as a white solid.

후처리

  1. washwashed with water (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC on Chiralpak AS,
  6. washeluting with 25% isopropyl alcohol/CO2

출처 및 근거

ORD 기록
ord-09ab891bd8c64b2896d066c0de5b1620
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273749B2

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