Pyridine → 6-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole

HRID 2423069Notes

Reaction equation

HRID 2423069 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[F:30])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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]2[C:5]([CH:6]=[N:7][N:8]2[C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:22]([F:30])[CH:23]=2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 247281116-bromo-4-methoxy-1H-indazole

Product 1

HCID 592729816-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazoleYield 65.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-4-(methyloxy)-1H-indazole (1.0 g, 4.40 mmol) in dichloromethane (50 mL) was added 4-benzyloxy-3-fluorobenzeneboronic acid (2.16 g, 8.80 mmol), pyridine (0.71 mL, 8.79 mmol), copper acetate (1.2 g, 6.62 mmol) and powdered 4A molecular sieves (2 g). The reaction mixture was stirred at room temperature in the presence of air for 5 days. Celite was added to the mixture and stirred for 10 mins then the mixture was filtered through a pad of celite and then the filtrate was washed with dichloromethane, then washed with water, dried over magnesium sulphate, filtered and concentrated. The product was purified by silica gel chromatography eluting with 5-30% ethyl acetate in hexane to yield the title compound (D9) (1.23 g).

Workup

  1. additionCelite was added to the mixture
  2. stirringstirred for 10 mins
  3. filtrationthe mixture was filtered through a pad of celite
  4. washthe filtrate was washed with dichloromethane
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by silica gel chromatography
  10. washeluting with 5-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ae7b455e86fd4df1b33485d1116785e9
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

Loading…