(4-Aminophenoxy)benzene → 4-(4-Phenoxyphenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile

HRID 989332Notes

Reaction equation

HRID 989332 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:3]=12.[O:17]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCCO)C>[O:17]([C:24]1[CH:25]=[CH:26][C:27]([NH:28][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]3[C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[O:12][C:3]=23)=[CH:29][CH:30]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 8764(4-Aminophenoxy)benzeneHCID 98993994-Chlorobenzo[4,5]furo[3,2-b]pyridine-3 carbonitrile

Product 1

HCID 102709274-(4-Phenoxyphenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 200 mg (0.88 mmol) of 4-chlorobenzo[4,5]furo[3,2-b]pyridine-3-carbonitrile and 180 mg (0.96 mmol) of 4-phenoxyaniline in 5 mL of 2-ethoxyethanol is heated at reflux temperature for 3 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is washed with saturated sodium bicarbonate, followed by brine, then dried over sodium sulfate and filtered through a pad of diatomaceous earth. Concentration in vacuo yields 115 mg (35%) of a beige solid, mp 175-179° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  4. washThe organic layer is washed with saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through a pad of diatomaceous earth
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-bd042e1ef94342ad852d3fcc52e5e18c
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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