1-Bromo-4-fluorobenzene → HCID 22349465, compound

HRID 896026Notes

Reaction equation

HRID 896026 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)=[CH:5][CH:4]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([O:7][C:6]4[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[CH:16][CH:15]=3)[CH:11]=[N:12]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzeneHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 223494441H-Indazole, 5-(4-methoxyphenoxy)-

Product 1

HCID 22349465HCID 22349465, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-(4-methoxy-phenoxy)-1H-indazole (0.25 grams, 1.0 mmol), 4-fluorobromobenzene (0.23 mL, 0.36 grams, 2.08 mmol), cuprous oxide (0.15 grams, 1.0 mmol), potassium carbonate (0.29 grams, 2.08 mmol) and N,N-dimethylacetamide (0.25 mL) was stirred at 160° C. for 3 hours. After cooling to room temperature, the mixture was diluted with water, extracted 3 times with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of ethyl acetate in hexanes (0-100%), affording 1-(4-Fluoro-phenyl)-5-(4-methoxy-phenoxy)-1H-indazole as a colorless solid. MS: 335.3 [M+H]+

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted 3 times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a gradient of ethyl acetate in hexanes (0-100%)

Sources & evidence

ORD record
ord-43ef23c68b3f47e19c6d0c611096fb78
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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