Water → HCID 10292411, compound

HRID 1860639Notes

Reaction equation

HRID 1860639 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:19][C:20]([CH3:26])([CH3:25])[CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.O.[CH3:28][N:29](C=O)C>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.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:28]([C:2]1[CH:3]=[C:4]([CH2:19][C:20]([CH3:26])([CH3:25])[CH2:21][C:22]([OH:24])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)#[N:29]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 10223945HCID 10223945, compound

Product 1

HCID 10292411HCID 10292411, compound

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst

Procedure

The final product of STEP 4, EXAMPLE 13 (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 reflux and was allowed to reflux 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 and dried over Na2SO4. The solid was filtered and the filtrate was concentrated. The cude product was purified by flash chromatography on silica gel (EA/Hexane/NH4OH:80/19.5/0.5) to give 181 mg of desired compound as oily gum. NMR spectrum was consistent for the proposed structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureto reflux for 20 hours under nitrogen atmosphere
  4. filtrationwas filtered through celite under vacuum
  5. concentrationThe filtrate was concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwas washed with a saturated solution of ammonium chloride
  8. dry with materialdried over Na2SO4
  9. filtrationThe solid was filtered
  10. concentrationthe filtrate was concentrated
  11. customThe cude product was purified by flash chromatography on silica gel (EA/Hexane/NH4OH:80/19.5/0.5)

Sources & evidence

ORD record
ord-04c4523118434baaaf079dc5f4c7004e
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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