Cesium carbonate → HCID 59496814, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:44])[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](Br)[CH:25]=[C:24]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:23]=2)[C:10]=1[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH3:2].[S:45]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46]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:44])[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]([C:47]3[CH:48]=[CH:49][S:45][CH:46]=3)[CH:25]=[C:24]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:23]=2)[C:10]=1[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH3:2]Participants
5
Procedure
A similar procedure as described in Example 43, step 4 was used, starting from 4-[3-[6-(3-benzyloxy-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (260 mg, 0.39 mmol), 3-thiophenylboronic acid (99 mg, 0.78 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73 mg, 0.1 mmol), and cesium carbonate (253 mg, 0.78 mmol) to obtain 4-[3-[6-(3-benzyloxy-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (165 mg, 67%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C40H48O7S (M+Na)+ 695.3013. found 695.3008.
Sources & evidence
- ORD record
- ord-2e98c827ac69457ba48a22ffa08663ca
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088936B2
Reaction notes
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