Potassium Phosphate, Tribasic → HCID 53327737, compound

HRID 2402318Notes

Reaction equation

HRID 2402318 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:43][N:44]1[C:52]2[C:47](=[CH:48][C:49](B3OC(C)(C)C(C)(C)O3)=[CH:50][CH:51]=2)[CH:46]=[CH:45]1.[O:62]1[CH:66]=[CH:65][CH:64]=[C:63]1[C:67]1[O:71][C:70]([NH:72][C:73]([C:75]2[CH:80]=[CH:79][CH:78]=[C:77](I)[CH:76]=2)=[O:74])=[N:69][N:68]=1>C(O)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:62]1[CH:66]=[CH:65][CH:64]=[C:63]1[C:67]1[O:71][C:70]([NH:72][C:73]([C:75]2[CH:80]=[CH:79][CH:78]=[C:77]([C:49]3[CH:48]=[C:47]4[C:52](=[CH:51][CH:50]=3)[N:44]([CH3:43])[CH:45]=[CH:46]4)[CH:76]=2)=[O:74])=[N:69][N:68]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 162177781-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 70941647HCID 70941647, compound

Product 1

HCID 53327737HCID 53327737, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Palladium acetate (177 mg, 0.79 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (751 mg, 1.58 mmol), tripotassium phosphate (3.34 g, 15.7 mmol), and 1-methylindole-5-boronic acid pinacol ester (3.04 g, 11.8 mmol) were added to a solution of N-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]-3-iodobenzenecarboxamide (3.00 g, 7.87 mmol) prepared in Reference Example 3 in 1-butanol (75 mL), followed by stirring at 100° C. overnight in an argon atmosphere. The reaction solution was concentrated. A saturated aqueous solution of sodium chloride was added to the residue, followed by extraction with methylene chloride and drying over anhydrous sodium sulfate. The solvent was distilled off, and methanol was added to the residue. The precipitated solid was filtered off. The residue obtained by distilling the solvent off was subjected to purification by silica gel column chromatography and recrystallization from methanol to obtain the title compound (1.10 g, 2.86 mmol) (yield: 36%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionA saturated aqueous solution of sodium chloride was added to the residue
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialdrying over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. additionmethanol was added to the residue
  7. filtrationThe precipitated solid was filtered off
  8. customThe residue obtained
  9. distillationby distilling the solvent
  10. customoff was subjected to purification by silica gel column chromatography and recrystallization from methanol

Sources & evidence

ORD record
ord-04c5a532719e432fb630cdf686c4870d
Source dataset
uspto-grants-2014_08
Patent number
US08796320B2

Reaction notes

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