Dimethyl Sulfoxide → ethyl 2-(1-oxo-6-vinylphthalazin-2(1H)-yl)acetate

HRID 587702

반응식

HRID 587702 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][N:7]=[CH:6]2)=[CH2:2].BrC1C=C2[C:22](=CC=1)[C:21](=[O:25])NN=C2.[C:26]([O-:29])([O-])=O.[K+].[K+].[CH3:32]S(C)=O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:13]=[C:9]1[C:10]2[C:5](=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:12][CH:11]=2)[CH:6]=[N:7][N:8]1[CH2:32][C:26]([O:25][CH2:21][CH3:22])=[O:29]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 115359186-Bromophthalazin-1(2h)-oneHCID 866751746-vinylphthalazine-1(2H)-one

생성물 1

HCID 86675173ethyl 2-(1-oxo-6-vinylphthalazin-2(1H)-yl)acetate수율 63%

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

반응 조건

온도
80 °C

실험 절차

6-Vinylphthalazine-1(2H)-one (BI27): A solution of 6-bromophthalazine-1(2H)-one (0.25 g, 1.11 mmol), potassium vinyl trifluoroborate (0.446 g, 3.33 mmol) and K2CO3 (0.46 g, 3.33 mmol) in DMSO (2 mL) was degassed with argon for 20 min at ambient temperature. PdCl2(dppf) (0.04 g, 0.055 mmol) was added at ambient temperature, and the reaction mixture was heated to 80° C. for 2 h. The reaction mixture was cooled to ambient temperature and filtered through Celite® bed under vacuum and washed with EtOAc. The reaction mixture was extracted with EtOAc and the combined EtOAc layer dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. The crude compound was purified by column chromatography (SiO2, 100-200 mesh; 50% EtOAc/petroleum ether) to afford the title compound as a brown solid (0.12 g, 63%): 1H NMR (400 MHz, DMSO-d6) δ 13.61 (br, 1H), 8.33 (m, 1H), 8.19 (m, 1H), 8.01 (m, 2H), 6.97 (m, 1H), 6.15 (m, 1H), 5.56 (d, J=10.8 Hz, 1H); ESIMS m/z 172.93 ([M+H]+); IR (thin film) 1748, 1655, 3241 cm−1.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered through Celite® bed under vacuum
  3. washwashed with EtOAc
  4. extractionThe reaction mixture was extracted with EtOAc
  5. dry with materialthe combined EtOAc layer dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford the crude product
  8. customThe crude compound was purified by column chromatography (SiO2, 100-200 mesh; 50% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-32552d9005bf486d94f1332cb99af3e9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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