Methoxyisopropylamine → HCID 86610350, compound

HRID 1941755Notes

Reaction equation

HRID 1941755 reaction equation
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.Cl[C:44]1[CH:49]=[C:48]([C:50]2[CH:55]=[CH:54][N:53]=[C:52]([Cl:56])[CH:51]=2)[CH:47]=[CH:46][N:45]=1.[NH2:57][CH:58]([CH3:62])[CH2:59][O:60][CH3:61].CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:56][C:52]1[CH:51]=[C:50]([C:48]2[CH:47]=[CH:46][N:45]=[C:44]([NH:57][CH:58]([CH3:62])[CH2:59][O:60][CH3:61])[CH:49]=2)[CH:55]=[CH:54][N:53]=1

Participants

7

Reactant 4

HCID 123458MethoxyisopropylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 51720972,2'-dichloro-4,4'-bipyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 86610350HCID 86610350, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Xantphos (32 mg), and Pd2(dba)3 (25 mg) were suspended in toluene (8 ml) and stirred under argon for 10 mins, then 2,2′-dichloro-[4,4′]-bipyridinyl (250 mg), 2-amino-1-methoxypropane (0.117 ml) and sodium tert-butoxide (150 mg) were added. The mixture stirred at 60° C. for 6 hours then cooled to room temp, poured onto water and extracted with ethyl acetate, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by passing the crude mixture down Kieselgel using a gradient of hexane and ethyl acetate as the eluent.

Workup

  1. stirringThe mixture stirred at 60° C. for 6 hours
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-02c8b15a9dad4a318dd81a2cb77af2ea
Source dataset
uspto-grants-2013_03
Patent number
US08389442B2

Reaction notes

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