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

HRID 1504208Notes

Reaction equation

HRID 1504208 reaction equation
[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

Participants

8

Reactant 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

Product 1

HCID 66960678HCID 66960678, compoundYield 25.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2372b2e0ad6249e882058b51d6e1c850
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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