1,4-Dioxane → HCID 123384422, compound

HRID 1893602Notes

Reaction equation

HRID 1893602 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:43])[C:11](=[O:42])[CH2:12][N:13]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][C:38]=1[CH3:39])[N:35]([CH3:40])[N:34]=[C:33]2I)[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH3:22])=[O:16].[CH3:44]B1OB(C)OB(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>C(OCC)(=O)C.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Cl-].[Cl-].[Pd+2]>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[N:10]([CH3:43])[C:11](=[O:42])[CH2:12][N:13]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][C:38]=1[CH3:39])[N:35]([CH3:40])[N:34]=[C:33]2[CH3:44])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH3:22])=[O:16]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 574072TrimethylboroxineHCID 123758635HCID 123758635, compound

Product 1

HCID 123384422HCID 123384422, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The compound (734 mg, 1.04 mmol) of step A, trimethylboroxin (0.19 ml, 1.36 mmol), bis(tricyclohexylphosphine)palladium(II) dichloride (139 mg, 0.188 mmol), and 1.27 mol/l aqueous potassium phosphate solution (2.50 ml, 3.18 mmol) were added to 1,4-dioxane (8 ml), and the mixture was heated under reflux for 10 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-methanol) to give the title compound (505 mg, yield 82%) as a colorless amorphous solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 hr
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-786ab708f6624b2fa8b4a5256c53b589
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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