Phenol → 3,6-dimethyl-4-phenoxy-1-(2,4,6-trimethylphenyl)-1H-pyrazolo-[3,4-b]pyridine

HRID 1067268Notes

Reaction equation

HRID 1067268 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[N:10]=[C:11]([CH3:12])[C:3]=12.N[C@@H](CC)CO.[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH3:12][C:11]1[C:3]2[C:4](=[N:5][C:6]([CH3:8])=[CH:7][C:2]=2[O:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:9]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[N:10]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 1200842-Amino-1-butanol, (+)-HCID 211929064-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 211929053,6-dimethyl-4-phenoxy-1-(2,4,6-trimethylphenyl)-1H-pyrazolo-[3,4-b]pyridineYield 14.5%

Conditions

Temperature
190 °C

Procedure

A mixture of 4-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine (300 mg, 1 mmol), (S)-2-amino-1-butanol (107 mg, 1.2 mmol) and phenol (188 mg, 2 mmol) was heated in 190° C. oil bath for 15 hours. The mixture was cooled, quenched with 2 N sodium hydroxide and extracted with chloroform. The organic layer was separated and neutralized with 2 N hydrochloride and water. The organic layer was dried and concentrated to give an oil residue. The residue was purified through silica gel column chromatography using chloroform as eluent to give 157 mg of starting material, and 52 mg of 3,6-dimethyl-4-phenoxy-1-(2,4,6-trimethylphenyl)-1H-pyrazolo-[3,4-b]pyridine as beige crystals. 1H NMR (CDCl3): 7.1-7.45 (m, 5H), 6.95 (s, 2H), 6.06 (s, 1H), 2.71 (s, 3H), 2.38 (s, 3H), 2.29 (S, 3H), 1.94 (s, 6H) ppm; and 30 mg of 2-[3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1-H-pyrazolo[3,4-b]pyridin4-ylamino]-butan-1-olasa yellow glass.

Workup

  1. temperatureThe mixture was cooled
  2. customquenched with 2 N sodium hydroxide
  3. extractionextracted with chloroform
  4. customThe organic layer was separated
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto give an oil residue
  8. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-e63c2c29d7c34fad83c6f852589e9303
Source dataset
uspto-grants-2001_06
Patent number
US06248753B1

Reaction notes

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