Isopropyl iodide → HCID 22349437, compound

HRID 896028Notes

Reaction equation

HRID 896028 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.[H-].[Na+].I[CH:22]([CH3:24])[CH3:23]>CN(C)C=O.O>[CH:22]([N:13]1[C:14]2[C:10](=[CH:9][C:8]([O:7][C:6]3[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:16][CH:15]=2)[CH:11]=[N:12]1)([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 223494441H-Indazole, 5-(4-methoxyphenoxy)-

Product 1

HCID 22349437HCID 22349437, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-methoxy-phenoxy)-1H-indazole (0.20 grams, 0.83 mmol) in 1 mL of dimethylformamide was added sodium hydride (0.040 grams of a 60% dispersion in mineral oil, 1.0 mmol). After shaking at room temperature for 10 minutes, the mixture was treated with 2-iodopropane (0.090 mL, 0.15 grams, 0.9 mmol). The mixture was heated to 50° C. for 6 hours. After cooling to room temperature, the mixture was diluted with water and was extracted 3 times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0-30% ethyl acetate in hexanes, affording 1-isopropyl-5-(4-methoxy-phenoxy)-1H-indazole (90 miligrams) MS: 283.4 [M+H]+ and 2-isopropyl-5-(4-methoxy-phenoxy)-2H-indazole MS: 283.4 [M+H]+ (75 miligrams) as colorless syrup.

Workup

  1. temperatureThe mixture was heated to 50° C. for 6 hours
  2. temperatureAfter cooling to room temperature
  3. extractionwas extracted 3 times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f75625843fea420da93dc9d0093428fe
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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