Pyridine → 5-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole

HRID 2423077Notes

Reaction equation

HRID 2423077 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[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(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:24]1[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]=1)[N:6]=[CH:5]2

Participants

7

Reactant 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 231345645-bromo-4-methoxy-1H-indazole

Product 1

HCID 592729765-Bromo-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazoleYield 51.6%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-4-(methyloxy)-1H-indazole (D19) (0.670 g, 2.95 mmol), 4-benzyloxy-3-fluorobenzeneboronic acid (1.45 g, 5.90 mmol), copper (II) acetate (0.804 g, 4.43 mmol), pyridine (0.447 mL, 5.90 mmol) and powdered 4A molecular sieves (3 g) in dichloromethane (30 mL) was stirred in an air atmosphere at room temperature. After 4 days, the mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water, dried (Na2SO4) and concentrated. Chromatography on silica gel (0-30% ethyl acetate in hexane and diethyl ether in hexane) gave the title compound (D20) (0.65 g)

Workup

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b8d9204dcb6e4f76b1100dc3f54f3dc4
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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