Cesium carbonate → HCID 57863025, compound

HRID 418106Notes

Reaction equation

HRID 418106 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[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][CH3:32])(=[O:30])=[O:29])[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:2].[F:42][C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][C:44]=1[OH:52].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:41])[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:46]3[CH:47]=[CH:48][C:43]([F:42])=[C:44]([OH:52])[CH:45]=3)[CH:25]=[C:26]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])[CH:27]=2)[C:10]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 44717470(4-Fluoro-3-hydroxyphenyl)boronic acidHCID 57863128HCID 57863128, compound

Product 1

HCID 57863025HCID 57863025, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

A similar procedure as described in Example 41, step 1 was used, starting from 4-[3-[6-(3-bromo-5-ethanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (213 mg, 0.32 mmol), 4-fluoro-3-hydroxy-phenylboronic acid (101 mg, 0.64 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (37 mg, 0.05 mmol), and cesium carbonate (317 mg, 0.97 mmol) to afford 4-[3-[6-(5-ethanesulfonyl-4′-fluoro-3′-hydroxy-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (218 mg, 99%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C37H47FO9S (M+Na)+ 709.2817, found 709.2817.

Sources & evidence

ORD record
ord-8886261d828f445ca757e8e0095fd66b
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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