Pyridine → HCID 131724969, compound

HRID 1070409Notes

Reaction equation

HRID 1070409 reaction equation
[NH2:1]C1C=CC(C2C=CC=CC=2)=CC=1C#N.N1C=CC=CC=1.[C:22](Cl)(Cl)=[O:23].[C:26]1([C:32]2[CH:33]=[CH:34][C:35]3[O:39][C:38]([CH2:40][OH:41])=[CH:37][C:36]=3[CH:42]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:26]1([C:32]2[CH:33]=[CH:34][C:35]3[O:39][C:38]([CH2:40][O:41][C:22](=[O:23])[NH2:1])=[CH:37][C:36]=3[CH:42]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 6371PhosgeneHCID 8471TriethylamineHCID 9855722HCID 9855722, compoundHCID 113790942-Hydroxymethyl-5-phenyl-benzofuran

Product 1

HCID 131724969HCID 131724969, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-amino-biphenyl-3-carbonitrile (1.2 g, 6.33 mmol) and pyridine (2 mL, 25.3 mmol) was added 20% phosgene in toluene (5.7 mL(10.8 mmol) and the mixture was heated to 90° C. for 2 hrs. The mixture was filtered and the filtrate was concentrated to dryness. The crude material was dissolved in THF, and (5-phenyl-benzofuran-2-yl)-methanol (0.52 g, 2.3 mmol) and triethylamine (0.70 g, 6.9 mmol) were added. The mixture was heated at 50° C. for 15 h. The solvent was evaporated to dryness. Purification by chromatography gave 0.78 g of 3-cyano-biphenyl-4-yl)-carbamic acid-5-phenyl-benzofuran-2-yl-methyl ester as a light yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. dissolutionThe crude material was dissolved in THF
  4. temperatureThe mixture was heated at 50° C. for 15 h
  5. customThe solvent was evaporated to dryness
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-666cc9a4d0854affa00fa834defaaf51
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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