Potassium Carbonate → [2-(1-Benzyl-1H-pyrazol-4-yl)-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone
Reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[CH2:11]([N:18]1[CH:22]=[C:21]([C:23]#[CH:24])[CH:20]=[N:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29](I)[CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34].[C:38](=O)([O-])[O-:39].[K+].[K+]>CO.C(OCC)(=O)C>[CH2:11]([N:18]1[CH:22]=[C:21]([C:23]2[O:10][C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[C:24]=2[C:38]([C:29]2[CH:28]=[C:27]([O:26][CH3:25])[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=2)=[O:39])[CH:20]=[N:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
This compound was prepared by application of the general procedure to 2-iodo-5-methoxy-phenol, 1-benzyl-4-ethynyl-1H-pyrazole and 3,4,5-trimethoxy-iodo-benzene. The crude product was stirred with potassium carbonate (excess) in methanol to hydrolyse ester by-products and submitted to silica-gel flash chromatography (eluent=2:1 hexanes:ethyl acetate) to afford the title compound as a yellow resin that crystallised after trituration in diethyl ether (31% yield). An analytical sample was obtained by preparative thin layer chromatography (eluent=2:1 hexane: ethyl acetate). 1H-NMR (CDCl3) δ 8.10 (s, 1H), 8.03 (s, 1H), 7.36-7.21 (m, 5H), 7.13 (d, J=8.7 Hz, 1H), 7.11 (s, 2H), 7.03 (d, J=2.0 Hz, 1H), 6.79 (dd, J 8.7, 2.0 Hz, 1H), 5.29 (s, 2H), 3.92 (s, 3H), 3.85 (s, 3H), 3.75 (s, 6H). 13C—NMR (CDCl3) δ 190.3, 158.2, 154.3, 153.3, 153.0, 142.4, 139.3, 135.7, 133.7, 130.3, 128.9, 128.3, 127.8, 121.8, 120.9, 114.0, 113.1, 112.3, 107.1, 95.6, 61.1, 56.4, 56.3, 55.8.
Sources & evidence
- ORD record
- ord-40903400bd634a5ba5286043893e6122
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278290B2
Reaction notes
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