Water → HCID 12018745, compound

HRID 1860690Notes

Reaction equation

HRID 1860690 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([CH3:28])([CH3:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].O.[CH3:30][N:31](C=O)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].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:30]([C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:5]=[CH:4][C:3]=1[CH2:19][C:20]([CH3:28])([CH3:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])#[N:31]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 12018744HCID 12018744, compound

Product 1

HCID 12018745HCID 12018745, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
120 °C

Procedure

Ethyl 4-{2-bromo-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoate (500 mg) was dissolved in DMF (10 mL) and water (1.0 mL) and was treated with tris(dibenzylideneacetone)dipalladium(0) (51 mg) and bis(diphenylphosphino)ferrocene (75 mg). The reaction mixture was heated to 120° C. for 20 hours under nitrogen atmosphere. The mixture was cooled to room temperature and was filtered through Celite under vacuum. The filtrate was concentrated. The residue was dissolved in ethyl acetate and was washed with a saturated solution of ammonium chloride, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (EA/Hexane: 40/60) to give 390 mg (88.6%) of the desired compound as an oily gum. NMR spectrum was consistent for the proposed structure.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationwas filtered through Celite under vacuum
  3. concentrationThe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwas washed with a saturated solution of ammonium chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (EA/Hexane: 40/60)

Sources & evidence

ORD record
ord-9eaee701f7494493af1e8279bc15b60a
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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