Pyridine → HCID 59272968, compound

HRID 2423067Notes

Reaction equation

HRID 2423067 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][C:21]=1[F:29])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:23]1[CH:24]=[CH:25][C:20]([O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:21]([F:29])[CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 247287454-Bromo-6-fluoro-1H-indazole

Product 1

HCID 59272968HCID 59272968, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-6-fluoro-1H-indazole (1.0 g, 4.65 mmol) in dichloromethane (50 mL) was added 4-benzyloxy-3-fluorobenzeneboronic acid (2.29 g, 9.31 mmol), pyridine (0.75 mL, 9.28 mmol), copper acetate (1.26 g, 6.96 mmol) and powdered 4A molecular sieves (2 g). The reaction mixture was stirred at room temperature in the presence of air for 4 days. Celite was added to the mixture and stirred for 5 mins, then the mixture was filtered through a pad of celite and then the filtrate was washed with water, dried over magnesium sulphate, filtered and concentrated. The product was purified by silica gel chromatography eluting with 5-100% dichloromethane in hexane to yield the title compound (D7) (779 mg).

Workup

  1. additionCelite was added to the mixture
  2. stirringstirred for 5 mins
  3. filtrationthe mixture was filtered through a pad of celite
  4. washthe filtrate was washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by silica gel chromatography
  9. washeluting with 5-100% dichloromethane in hexane

Sources & evidence

ORD record
ord-a5ec9412c4b542809de3862c051e81dd
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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