Potassium Phosphate, Tribasic → HCID 58767470, compound

HRID 639933Notes

Reaction equation

HRID 639933 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([N:14]2[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]2)=[N:4][C:3]=1[C:20]#[N:21].[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]([N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1)=[N:4][C:3]([C:20]#[N:21])=[C:2]2[C:24]1[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 68518318HCID 68518318, compound

Product 1

HCID 58767470HCID 58767470, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-chloro-6-methoxy-1-(4-methyl-1H-imidazol-1-yl)isoquinoline-3-carbonitrile (0.055 g, 0.184 mmol), 3-pyridylboronic acid (0.034 g, 0.276 mmol), Pd2(dba)3 (0.017 g, 0.018 mmol), tricyclohexylphosphene (0.015 g, 0.055 mmol) and K3PO4 (0.117 g, 0.552 mmol) were taken in 7 mL dry dioxane and heated at 100° C. under argon atmosphere for 22 h. The reaction mixture was filtered through celite and concentrated. To the resulting residue all of the above reagents and 6 mL dioxane were added and then the mixture was heated at 100° C. for 22 h. The reaction was cooled to rt, filtered through celite (washing with CH2Cl2) and the filtrate was concentrated, then purified by flash chromatography: 3% to 6% MeOH—NH4OH (90:10, v/v) in EtOAc. Irnpure fractions from the flash chromatography were combined and purified by reverse phase HPLC to give a white solid (0.025 g, 40%).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated
  3. additionTo the resulting residue all of the above reagents and 6 mL dioxane were added
  4. temperaturethe mixture was heated at 100° C. for 22 h
  5. temperatureThe reaction was cooled to rt
  6. filtrationfiltered through celite (washing with CH2Cl2)
  7. concentrationthe filtrate was concentrated
  8. custompurified by flash chromatography
  9. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-284094eadc5b4ba28ebc3593a0ede192
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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