Potassium Carbonate → HCID 67976104, compound

HRID 706549Notes

Reaction equation

HRID 706549 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:19]=[C:18]([CH3:20])[N:17]([CH:21]([CH3:23])[CH3:22])[N:16]=2)[N:3]=1.[C:24]([O-])([O-])=O.[K+].[K+].CB(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+]>C(O[Pd]OC(=O)C)(=O)C.O1CCOCC1.O>[CH:21]([N:17]1[C:18]([CH3:20])=[CH:19][C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:24])=[N:3]2)=[N:16]1)([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateHCID 86699322HCID 86699322, compound

Product 1

HCID 67976104HCID 67976104, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A flask was charged with 1,4-dioxane/H2O (30 mL/5 mL). The flask was cooled to 0° C. and vacuum was applied for 20 minutes. A second flask was charged with 3-bromo-1-((1-isopropyl-5-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (1.95 g, 5.16 mmol), K2CO3 (2.85 g, 20.6 mmol), diacetoxypalladium (0.0579 g, 0.258 mmol), methylboronic acid (0.926 g, 15.5 mmol) and sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate (0.264 g, 0.516 mmol). The second flask was evacuated with and back filled with nitrogen three times. The cold degassed dioxane/H2O was added to the second flask, which was evacuated and back filled with argon 5 times. The reaction mixture was heated to 80° C. for 3 hours. The reaction was cooled to ambient temperature and filtered, and concentrated under reduced pressure. The residue was diluted with EtOAc (200 mL). The organic layer was washed with saturated NaHCO3 (30 mL), dried (Na2SO4) and concentrated to give 1.34 g (83%) of the title compound, which was used in the next step without further purification.

Workup

  1. customThe second flask was evacuated with and
  2. additionback filled with nitrogen three times
  3. customThe cold degassed dioxane/H2O
  4. additionwas added to the second flask, which
  5. customwas evacuated
  6. additionback filled with argon 5 times
  7. temperatureThe reaction mixture was heated to 80° C. for 3 hours
  8. temperatureThe reaction was cooled to ambient temperature
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. additionThe residue was diluted with EtOAc (200 mL)
  12. washThe organic layer was washed with saturated NaHCO3 (30 mL)
  13. dry with materialdried (Na2SO4)
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-e255e00494594d4ca41674d5feb9546a
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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