Pyridine → 4-Bromo-1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole-6-carbonitrile

HRID 2423090Notes

Reaction equation

HRID 2423090 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[C:18]([F:28])[C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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]([C:11]#[N:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:16]1[CH:17]=[C:18]([F:28])[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:14]([F:13])[CH:15]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 247289174-Bromo-1H-indazole-6-carbonitrileHCID 54758874(4-(Benzyloxy)-3,5-difluorophenyl)boronic acid

Product 1

HCID 672458554-Bromo-1-{3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazole-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-1H-indazole-6-carbonitrile (1.0 g, 4.50 mmol) in dichloromethane (50 mL) was added {3,5-difluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid {DE 4236105} (1.8 g, 6.82 mmol), pyridine (0.73 mL, 9.04 mmol), copper acetate (1.22 g, 6.74 mmol) and powdered 4A molecular sieves (5 g). The reaction mixture was stirred at room temperature in the presence of air for 6 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 10-100% ethyl acetate in hexane to yield the title compound (D36) (944 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 10-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f6756b56569146e2aebdfdc548a81dcc
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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