4-Chloro-2-fluoroaniline → 4-(4-Chloro-2-fluorophenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile

HRID 2213774Notes

Reaction equation

HRID 2213774 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.[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([F:25])[CH:19]=1.Cl.N1C=CC=CC=1>C(OCCO)C>[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][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)=[C:20]([F:25])[CH:19]=1

Participants

5

Reactant 3

HCID 938984-Chloro-2-fluoroanilineHCID 98993994-Chlorobenzo[4,5]furo[3,2-b]pyridine-3 carbonitrileHCID 10176127Pyridinium chloride

Product 1

HCID 108822964-(4-Chloro-2-fluorophenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrileYield 40.4%

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 0.11 mL (0.97 mmol) of 4-chloro-2-fluoroaniline in 6 mL of 2-ethoxyethanol is heated at reflux temperature for 4 days. A catalytic amount of pyridine hydrochloride is added and the reaction mixture is heated at reflux temperature overnight then cooled to room temperature. The reaction mixture is partitioned between ethyl acetate and water. The organic layer is dried over sodium sulfate, filtered through a pad of diatomaceous earth and concentrated in vacuo to provide 120 mg (40%) of a beige solid, mp 259–261° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 days
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux temperature overnight
  5. customThe reaction mixture is partitioned between ethyl acetate and water
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered through a pad of diatomaceous earth
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be93e41851364b6690b115dfb5d98055
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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