Pyridine → 5-Bromo-3-methyl-1-phenyl-1H-indazole

HRID 1097006Notes

Reaction equation

HRID 1097006 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[CH3:12].N1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl[CH2:20]Cl>CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:14]1[CH:20]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:7]=[C:6]2[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 178434226HCID 178434226, compound

Product 1

HCID 579310235-Bromo-3-methyl-1-phenyl-1H-indazole

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

The mixture of 5-bromo-3-methyl-1H-indazole hydrochloride (999 mg), Cu(OAc)2 (1.13 g), pyridine (978 ul) and phenylbronic acid (982 mg) in dichloromethane (20 ml) was stirred at room temperature for over night. The mixture was filtered with celite pad, and the filtrate was evaporated under reduced pressure. The green residue was purified by silica gel chromatography (hexane/EtOAc) to give the intended compound as brown oil.

Workup

  1. filtrationThe mixture was filtered with celite pad
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe green residue was purified by silica gel chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-273e0ceaffe24067a40b6441f3490ab4
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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