[2-(1-benzyl-1H-pyrazol-4-yl)-7-benzyloxy-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone → [7-Hydroxy-6-methoxy-2-(1H-pyrazol-4-yl)-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone
Reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]2[O:14][C:15]3[C:35]([O:36]CC4C=CC=CC=4)=[C:34]([O:44][CH3:45])[CH:33]=[CH:32][C:16]=3[C:17]=2[C:18]([C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)=[O:19])[CH:10]=[N:9]1)C1C=CC=CC=1>[Pd].Cl.C(OCC)(=O)C.CO>[OH:36][C:35]1[C:15]2[O:14][C:13]([C:11]3[CH:10]=[N:9][NH:8][CH:12]=3)=[C:17]([C:18]([C:20]3[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=3)=[O:19])[C:16]=2[CH:32]=[CH:33][C:34]=1[O:44][CH3:45]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
A suspension of crude [2-(1-benzyl-1H-pyrazol-4-yl)-7-benzyloxy-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone (29 mg), 10% palladium on carbon (20 mg) and 6M HCl(aq) (2 drops) in ethyl acetate (2 mL) and methanol (1 mL) was stirred at room temperature overnight. After this time the reaction mixture was filtered through celite and the solvent removed under vacuum. The crude residue was purified by preparative thin layer chromatography to afford the product as a pale yellow resin that was solidified by freeze-drying with t-butanol (5 mg, 2% over two steps).
Workup
- filtrationAfter this time the reaction mixture was filtered through celite
- customthe solvent removed under vacuum
- customThe crude residue was purified by preparative thin layer chromatography
- customto afford the product as a pale yellow resin that
- dry with materialby freeze-drying with t-butanol (5 mg, 2% over two steps)
Sources & evidence
- ORD record
- ord-722ad30a0354446abdb348381024f45d
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278290B2
Reaction notes
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