Pyridine → 1-(4-Methoxyphenyl)-4-(phenylmethoxy)-1H-indazole

HRID 2423086Notes

Reaction equation

HRID 2423086 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[N:12][NH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:13]2[C:14]3[C:10](=[C:9]([O:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 231344734-(Benzyloxy)-1h-indazole

Product 1

HCID 592729721-(4-Methoxyphenyl)-4-(phenylmethoxy)-1H-indazoleYield 21.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

The 4-[(phenylmethyl)oxy]-1H-indazole (D1) (543 mg, 1.65 mmol), the [4-(methyloxy)phenyl]boronic acid (500 mg, 3.29 mmol), copper (II) acetate (448 mg, 2.47 mmol), powdered molecular sieves (400 mg) and pyridine (0.27 mL, 3.29 mmol) in DCM (75 mL) were stirred at room temperature in the presence of air. After 4 hours the mixture was filtered through a pad of celite and washed with water. The aqueous was re-extracted with DCM and the combined organics were washed with brine and dried over MgSO4. The crude (880 mg) was purified by flash chromatography (Biotage SP4) with a gradient of Et2O (0 to 30%) in hexane to afford 115 mg of title compound (D32).

Workup

  1. filtrationAfter 4 hours the mixture was filtered through a pad of celite
  2. washwashed with water
  3. extractionThe aqueous was re-extracted with DCM
  4. washthe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude (880 mg) was purified by flash chromatography (Biotage SP4) with a gradient of Et2O (0 to 30%) in hexane

Sources & evidence

ORD record
ord-a7c699bfc0e04a1790fdddb82485adb7
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

Loading…