Cesium carbonate → methyl 2-{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate
Reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][CH:4]=[C:3]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([OH:23])[CH:17]=[CH:16]2.[CH3:24][O:25][C:26](=[O:43])[CH:27](OS(C(F)(F)F)(=O)=O)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=[C:3]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([O:23][CH:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26]([O:25][CH3:24])=[O:43])[CH:17]=[CH:16]2Participants
Procedure
In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.300 g, 1.00 mmol), prepared in step 2 of Example 5, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.469 g, 1.50 mmol) and cesium carbonate (0.653 g, 2.00 mmol) with the exception that this reaction was complete after 4 hours at ambient temperature. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 25% to 55% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.437 g, 94%), mp 117–118° C. Elemental Analysis for C31H27NO3 Calc'd: C, 80.67; H, 5.90; N, 3.03. Found: C, 80.35; H, 6.16; N, 2.91.
Workup
- customPurification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å)
Sources & evidence
- ORD record
- ord-b8a75a9e4d7142afa038a16869fe334f
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186749B2
Reaction notes
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