1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 66960678, 화합물

HRID 1504208노트

반응식

HRID 1504208 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[C:11](=[O:17])[CH:10]=[CH:9]2.Br[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([O:29][CH3:30])=[N:21][CH:20]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH3:30][O:29][C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH3:16])[C:11](=[O:17])[CH:10]=[CH:9]3)=[CH:20][N:21]=1

참가 물질

8

반응물 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 247666564-Bromo-1-methoxyisoquinolineHCID 669605486-(3-aminopropoxy)-1-methyl-1H-quinolin-2-one

생성물 1

HCID 66960678HCID 66960678, 화합물수율 25.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

6-(3-Amino-propoxy)-1-methyl-1H-quinolin-2-one(232 mg), 4-bromo-1-methoxy-isoquinoline(286 mg), palladium acetate (II) (22 mg), xantphos (558 mg), and sodium t-butoxide(192 mg) were added to dioxane(10 ml). The mixture was heated at 80° C. for overnight under argon atmosphere. The reaction liquid was cooled to room temperature. Water was added to the reaction mixture, and followed by celite filtration. The filtrate was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate: hexane=2:1→1:0). The purified product was condensed under reduced pressure to give the title compound(99 mg) as a brown amorphous solid.

후처리

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. filtrationfollowed by celite filtration
  4. extractionThe filtrate was extracted with dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customcondensed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate: hexane=2:1→1:0)
  8. customcondensed under reduced pressure

출처 및 근거

ORD 기록
ord-2372b2e0ad6249e882058b51d6e1c850
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212187B2

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