Pyridine → HCID 59272962, compound

HRID 2423079Notes

Reaction equation

HRID 2423079 reaction equation
[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:13]([F:12])[CH:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 59272978HCID 59272978, compound

Product 1

HCID 59272962HCID 59272962, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromo-5-chloro-1H-indazole (D22) (0.361 g, 1.56 mmol), {3-fluoro-4-[(phenylmethyl)oxy]phenyl}boronic acid (0.57 g, 2.32 mmol), copper (II) acetate (0.42 g, 2.31 mmol) and pyridine (0.25 mL, 3.10 mmol) in dichloromethane (50 mL) were stirred together vigorously under an air atmosphere with powdered 4A molecular sieves (1.5 g). After 5 days, the mixture was filtered through celite and the solvent evaporated. The concentrate was chromatographed (silica, dichloromethane/hexane) to give the title compound (D23) as an off white solid (0.32 g)

Workup

  1. filtrationthe mixture was filtered through celite
  2. customthe solvent evaporated
  3. customThe concentrate was chromatographed (silica, dichloromethane/hexane)

Sources & evidence

ORD record
ord-23b3685f2f474e30b6946d5d60b13c34
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

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