Cesium carbonate → HCID 57863120, compound

HRID 418112Notes

Reaction equation

HRID 418112 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].[S:42]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43]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: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:44]3[CH:45]=[CH:46][S:42][CH:43]=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 581760Thiophene-3-boronic acidHCID 57863128HCID 57863128, compound

Product 1

HCID 57863120HCID 57863120, compoundYield 77.2%

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 (154 mg, 0.23 mmol), 3-thiopheneboronic acid (60.2 mg, 0.47 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (26 mg, 0.035 mmol), and cesium carbonate (155 mg, 0.47 mmol) to afford 4-[3-[6-(3-ethanesulfonyl-5-thiophen-3-yl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (117 mg, 76%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C35H46O8S2 (M+Na)+ 681.2526, found 681.2526.

Sources & evidence

ORD record
ord-90c56c6af9d0420cbecaf41fe710f00e
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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