Pyridine → 3-(5-Phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid ethyl ester
Reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH2:13])=[O:6])[CH3:3].N1C=CC=CC=1.[C:20](Cl)(Cl)=[O:21].[C:24]1([C:30]2[CH:31]=[CH:32][C:33]3[O:37][C:36]([CH2:38][OH:39])=[CH:35][C:34]=3[CH:40]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:2]([O:4][C:5](=[O:6])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH:13][C:20]([O:39][CH2:38][C:36]1[O:37][C:33]2[CH:32]=[CH:31][C:30]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:40][C:34]=2[CH:35]=1)=[O:21])[CH3:3]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of ethyl-3-aminopyridine-4-carboxylate hydrochloride (1.0 g, 4.93 mmol) and pyridine (1.2 ml, 14.8 mmol) in toluene (10 ml) at room temperature under argon was added 20% phosgene in toluene (3.7 ml, 7.15 mmol) and the mixture was heated at 90° C. for 1 h. The mixture was filtered, and the filtrate was concentrated to dryness. The crude material was dissolved in toluene (10 ml), (5-phenyl-benzofuran-2-yl)-methanol (0.922 g, 4.11 mmol) and DMAP (0.05 g, 0.411 mmol) were added and the mixture was heated at 90° C. for 18 h. The solvent was evaporated to dryness. Purification by chromatography gave 0.538 g of 3-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-isonicotinic acid ethyl ester as a white solid.
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated to dryness
- dissolutionThe crude material was dissolved in toluene (10 ml)
- temperaturethe mixture was heated at 90° C. for 18 h
- customThe solvent was evaporated to dryness
- customPurification by chromatography
Sources & evidence
- ORD record
- ord-01dc848f246b48aab8c09e59509a24bf
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06569860B2
Reaction notes
Loading…