Cesium carbonate → HCID 59496806, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:43])[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]([O:28][CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:2].[F:44][C:45]1[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][CH:50]=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:43])[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:49]3[CH:48]=[CH:47][CH:46]=[C:45]([F:44])[CH:50]=3)[CH:25]=[C:26]([O:28][CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:27]=2)[C:10]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:2]Participants
5
Procedure
A similar procedure as described in Example 43, step 4 was used, starting from 4-[3-[6-(3-bromo-5-cyclopentylmethoxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (152 mg, 0.23 mmol), 3-fluorophenylboronic acid (65 mg, 0.46 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73 mg, 0.1 mmol), and cesium carbonate (150 mg, 0.46 mmol) to obtain 4-[3-[6-(5-cyclopentylmethoxy-3′-fluoro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (114 mg, 74%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C41H53FO7 (M+H)+ 677.3848. found 677.3850.
Sources & evidence
- ORD record
- ord-e1f8fcdd195e48ae9c9bdaa05c31ec72
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088936B2
Reaction notes
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