Cesium carbonate → HCID 67339942, compound

HRID 1670125Notes

Reaction equation

HRID 1670125 reaction equation
C(OC(=O)CCCOC1C=CC=C(CCCCCCOC2C=C(C3C=CC(F)=C(F)C=3)C=C(C(=O)N(C)C)C=2)C=1CCC(OCC)=O)C.[CH2:49]([O:51][C:52](=[O:93])[CH2:53][CH2:54][CH2:55][O:56][C:57]1[CH:62]=[CH:61][CH:60]=[C:59]([CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][O:69][C:70]2[CH:75]=[C:74]([C:76]([N:78]3[CH2:82][CH2:81][C:80]([F:84])([F:83])[CH2:79]3)=[O:77])[CH:73]=[C:72](Br)[CH:71]=2)[C:58]=1[CH2:86][CH2:87][C:88]([O:90][CH2:91][CH3:92])=[O:89])[CH3:50].[S:94]1[CH:98]=[CH:97][C:96](B(O)O)=[CH:95]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.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]>[CH2:49]([O:51][C:52](=[O:93])[CH2:53][CH2:54][CH2:55][O:56][C:57]1[CH:62]=[CH:61][CH:60]=[C:59]([CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][O:69][C:70]2[CH:71]=[C:72]([C:96]3[CH:97]=[CH:98][S:94][CH:95]=3)[CH:73]=[C:74]([C:76]([N:78]3[CH2:82][CH2:81][C:80]([F:84])([F:83])[CH2:79]3)=[O:77])[CH:75]=2)[C:58]=1[CH2:86][CH2:87][C:88]([O:90][CH2:91][CH3:92])=[O:89])[CH3:50]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 581760Thiophene-3-boronic acidHCID 67337985HCID 67337985, compoundHCID 67339165HCID 67339165, compound

Product 1

HCID 67339942HCID 67339942, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared by the same method as 4-{3-[6-(5-dimethylcarbamoyl-3′,4′-difluoro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester starting from 4-[3-{6-[3-bromo-5-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (114 mg, 0.163 mmol), thiophen-3-ylboronic acid (42.57 mg, 0.326 mmol), PdCl2(dppf) (17.94 mg, 0.025 mmol) and cesium carbonate (107.5 mg, 0.326 mmol) in dimethoxyethane (3.7 mL) to obtain 4-[3-{6-[3-(3,3-difluoro-pyrrolidine-1-carbonyl)-5-thiophen-3-yl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (90 mg, 79%) as a colorless oil.

Sources & evidence

ORD record
ord-80b71ea4f60e4802a84efc917f414b5b
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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