Potassium Phosphate, Tribasic → 2,3-dimethyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole

HRID 902539Notes

Reaction equation

HRID 902539 reaction equation
Br[C:2]1[C:10]2[C:6](=[C:7]([CH3:12])[N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:15]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][N:8]1[C:7]([CH3:12])=[C:6]2[C:10]([C:2]([C:15]3[C:16]([CH3:21])=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=3[CH3:13])=[CH:3][CH:4]=[CH:5]2)=[N:9]1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 441194737-Bromo-2,3-dimethyl-2H-indazole

Product 1

HCID 588610082,3-dimethyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

A flask containing 7-bromo-2,3-dimethyl-2H-indazole (3.23 g, 14.4 mmol), 2,4,6-trimethylphenyl boronic acid (3.51 g, 21.4 mmol), freshly ground potassium phosphate (6.04 g, 28.5 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.225 g, 0.572 mmol), and palladium(II) acetate (0.032 g, 0.14 mmol) was evacuated and back-filled with nitrogen. Toluene (50 mL) was added, and the yellow-orange mixture was stirred at 100° C. for 22 h then allowed to cool. Ether (200 mL) was added, and the yellow solution was decanted from a dark granular solid. The organic layer was sequentially washed with 200 mL of a 10% aqueous NaOH solution and 200 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a pale yellow solid. Column chromatography (0→33% EtOAc/hexanes) afforded 2,3-dimethyl-7-(2,4,6-trimethyl-phenyl)-2H-indazole as an off-white solid (7: R=R′=Me, Ar=2,4,6-trimethylphenyl; 3.03 g, 79%; m.p. 162-164).

Workup

  1. customwas evacuated
  2. additionback-filled with nitrogen
  3. additionToluene (50 mL) was added
  4. temperatureto cool
  5. additionEther (200 mL) was added
  6. customthe yellow solution was decanted from a dark granular solid
  7. washThe organic layer was sequentially washed with 200 mL of a 10% aqueous NaOH solution and 200 mL of a saturated aqueous NaCl solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to a pale yellow solid

Sources & evidence

ORD record
ord-c44bf591ad4445368af7fa648eed8a54
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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