Cesium carbonate → HCID 57863115, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:42])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH2:31][CH2:32][CH3:33])(=[O:30])=[O:29])[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:2].[S:43]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4](=[O:42])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:45]3[CH:46]=[CH:47][S:43][CH:44]=3)[CH:25]=[C:26]([S:28]([CH2:31][CH2:32][CH3:33])(=[O:30])=[O:29])[CH:27]=2)[C:10]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:2]Participants
5
Procedure
A similar procedure as described in Example 41, step 1 was used, starting from 4-[2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-bromo-5-(propane-1-sulfonyl)-phenoxy)-hexyl]-phenoxy]-butyric acid ethyl ester (208 mg, 0.31 mmol), 3-thiopheneboronic acid (81.2 mg, 0.62 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (34 mg, 0.047 mmol), and cesium carbonate (205 mg, 0.62 mmol) to afford 4-[2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-(propane-1-sulfonyl)-5-thiophen-3-yl-phenoxy)-hexyl]-phenoxy]-butyric acid ethyl ester (152 mg, 73%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C36H48O8S2 (M+Na)+ 695.2683, found 695.2680.
Sources & evidence
- ORD record
- ord-ed574b5a856e40baa9c6e4376abfe570
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093253B2
Reaction notes
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