Sodium t-butoxide → 2-(4-methoxyphenyl)-2H-indazole

HRID 1013041Notes

Reaction equation

HRID 1013041 reaction equation
Br[C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][N:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[NH2:6].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([N:5]2[CH:4]=[C:3]3[C:15]([CH:16]=[CH:17][CH:18]=[CH:2]3)=[N:6]2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 23676156Sodium t-butoxideHCID 58948771N-(2-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine

Product 1

HCID 12147772-(4-methoxyphenyl)-2H-indazole

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2-(4-Methoxyphenyl)-2H-indazole was prepared according to Song and Yee (Org. Lett. 2000, 2, 519). To a solution of N-(2-bromobenzyl)-N-(4-methoxyphenyl)hydrazine (298 mg, 0.97 mmol) in toluene (3.5 mL) were added palladium acetate (11 mg, 0.05 mmol), 1,1′-bis(diphenylphosphino)ferrocene (46 mg, 0.075 mmol) and sodium tert-butoxide (140 mg, 1.46 mmol). The vial was capped and the reaction was stirred at 90° C. overnight. After the reaction was allowed to cool, it was filtered through a pad of silica and concentrated to give the desired product. The reaction was assumed to be quantitative. LC-MS (C14H12N2O calculated 224) m/z 225 (M+H).

Workup

  1. custom2-(4-Methoxyphenyl)-2H-indazole was prepared
  2. customThe vial was capped
  3. temperatureto cool
  4. filtrationit was filtered through a pad of silica
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2eecf719827f4ed4b8c7289e14cccd3f
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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