Potassium Phosphate, Tribasic → HCID 86650792, compound

HRID 1893609Notes

Reaction equation

HRID 1893609 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]([CH3:46])[C:11](=[O:45])[CH2:12][N:13]([C:30]1[CH:35]=[CH:34][C:33](B2OCC(C)(C)CO2)=[CH:32][C:31]=1[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].[CH3:47][O:48][C:49](=[O:57])[C:50]1[CH:55]=[CH:54][C:53](Br)=[N:52][CH:51]=1.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]([CH3:46])[C:11](=[O:45])[CH2:12][N:13]([C:30]1[CH:35]=[CH:34][C:33]([C:53]2[CH:54]=[CH:55][C:50]([C:49]([O:48][CH3:47])=[O:57])=[CH:51][N:52]=2)=[CH:32][C:31]=1[CH3:44])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:21][CH3:22])=[O:16]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 13349623Methyl 6-bromopyridine-3-carboxylateHCID 86650793HCID 86650793, compound

Product 1

HCID 86650792HCID 86650792, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The compound (510 mg, 0.802 mmol) obtained in step A, 6-bromonicotinic acid methyl ester (208 mg, 0.962 mmol), bis(tricyclohexylphosphine)palladium(II)dichloride (59 mg, 0.080 mmol) and 1.27 mol/l aqueous potassium phosphate solution (0.95 ml) were dissolved in 1,4-dioxane (4 ml), and the mixture was heated under reflux for 8 hr. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried over sodium 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 (375 mg, yield 71%) as a brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hr
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium 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-50426192cbe44f9a9997a0218d6e3e5b
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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