3-Bromoaniline → 4-(3-Bromophenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile

HRID 989331Notes

Reaction equation

HRID 989331 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.[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C(OCCO)C>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][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:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 98993994-Chlorobenzo[4,5]furo[3,2-b]pyridine-3 carbonitrile

Product 1

HCID 109705214-(3-Bromophenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrileYield 63.4%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 300 mg (1.30 mmol) of 4-chlorobenzo[4,5]furo[3,2-b]pyridine-3-carbonitrile and 0.160 mL (1.43 mmol) of 3-bromoaniline in 8 mL of 2-ethoxyethanol is heated at reflux temperature for 24 hours. The reaction mixture is 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, filtered through a pad of diatomaceous earth and concentrated in vacuo. The resultant solid is collected by filtration to give 300 mg (42%) of a beige solid, mp 242-245° C.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. customThe reaction mixture is partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic layer is washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered through a pad of diatomaceous earth
  6. concentrationconcentrated in vacuo
  7. filtrationThe resultant solid is collected by filtration

Sources & evidence

ORD record
ord-b2e5a98a6c8941f1ac2fb5c20131ae6a
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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