Dimethylacetamide → {1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037205노트

반응식

HRID 1037205 반응식
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24](Br)[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[C:38]([N:40](C)C)=O>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:38]#[N:40])[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 31374DimethylacetamideHCID 67067709{1-[4-(6-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

생성물 1

HCID 67067657{1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester수율 54%

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

반응 조건

온도
150 °C

실험 절차

{1-[4-(6-Bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (92 mg, 0.17 mmol), zinc (II) cyanide (40 mg, 0.34 mmol) and tetrakis(triphenyphosphine)palladium(0) (20 mg, 0.017 mmol) were suspended in DMA (2 mL) in a microwave vial. The vial was sealed, evacuated and flushed twice with nitrogen. The mixture was heated in a microwave at 150° C. for 30 min. The resulting mixture was allowed to cool to RT, partitioned between ethyl acetate (40 mL) and water (20 mL) and the phases separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (45 mg, 54%). LCMS (Method B): RT=4.76 min, [M+Na]+=515.

후처리

  1. customThe vial was sealed
  2. customevacuated
  3. customflushed twice with nitrogen
  4. temperatureto cool to RT
  5. custompartitioned between ethyl acetate (40 mL) and water (20 mL)
  6. customthe phases separated
  7. washThe organic layer was washed with brine (20 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d21b3ee55f9d4e9c9c802861c6829ffa
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

반응 노트

불러오는 중…