Potassium Phosphate, Tribasic → HCID 71254491, compound

HRID 540326Notes

Reaction equation

HRID 540326 reaction equation
Cl[C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][NH:22][C:21](=[O:24])[CH2:20][CH2:19][C:18]=2[CH:25]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:13][C:14]1[CH:15]=[CH:16][C:17]2[CH2:23][N:22]([C:2]3[CH:11]=[C:10]([Cl:12])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)[C:21](=[O:24])[CH2:20][CH2:19][C:18]=2[CH:25]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6075032,4-DichloroquinolineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 590157147-Bromo-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one

Product 1

HCID 71254491HCID 71254491, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2,4-dichloroquinoline (196 mg, 1.0 mmol) in dioxane (4 mL) was added 7-bromo-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one (161 mg, 1.0 mmol), followed by tris(dibenzylideneacetone)dipalladium(0) (28 mg, 0.03 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (65 mg, 0.11 mmol), and potassium phosphate tribasic (212 mg, 1.0 mmol). The resultant mixture was refilled with nitrogen and heated at 130° C. overnight. After cooled to room temperature, the mixture was diluted with acetonitrile (10 mL), filtered, and washed with acetonitrile. The filtrate was concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel (hexane/ethyl acetate/ammonium hydroxide solution, 80:19:1) to give 165 mg of product as a white solid (yield was 42%). MS obsd. (ESI+) [(M+H)+] 401.

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationfiltered
  3. washwashed with acetonitrile
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a residue which
  6. customwas purified by column chromatography on silica gel (hexane/ethyl acetate/ammonium hydroxide solution, 80:19:1)

Sources & evidence

ORD record
ord-1bcca9eb0cc2480a8c5dc11fa895136b
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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