Pyridine → 5-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-biphenyl-3-carboxylic Acid Methyl Ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4].N1C=CC=CC=1.[C:24](Cl)(Cl)=[O:25].[C:28]1([C:34]2[CH:35]=[CH:36][C:37]3[O:41][C:40]([CH2:42][OH:43])=[CH:39][C:38]=3[CH:44]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[C:9]([NH:11][C:24]([O:43][CH2:42][C:40]2[O:41][C:37]3[CH:36]=[CH:35][C:34]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[CH:44][C:38]=3[CH:39]=2)=[O:25])[CH:10]=1)=[O:4]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 5-amino-biphenyl-3-carboxylic acid methyl ester (crude from Step 4; 1.00 g, 4.40 mmol) and pyridine (0.711 mL, 8.80 mmol) in toluene (15 mL) at room temperature under argon was added 20% phosgene in toluene (3.3 mL, 6.3 mmol) and the mixture was heated at 90° C. for 1 h. The mixture was filtered, and the filtrate was concentrated to dryness (0.373 g). The crude material was dissolved in toluene (4 mL), (5-phenyl-benzofuran-2-yl)-methanol (0.300 g, 1.38 mmol) and DMAP (0.016 g, 0.137 mmol) were added and the mixture was heated at 90° C. for 18 h. The solvent was evaporated to dryness. Purification by flash chromatography gave 0.125 g of a white solid.
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated to dryness (0.373 g)
- dissolutionThe crude material was dissolved in toluene (4 mL)
- temperaturethe mixture was heated at 90° C. for 18 h
- customThe solvent was evaporated to dryness
- customPurification by flash chromatography
Sources & evidence
- ORD record
- ord-5d4413d2124348f68b1de28e01dcdc19
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06903086B2
Reaction notes
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