Cesium carbonate → Ethyl 3''-tert-butyl-4'-[4-(tert-butyldimethylsilanyloxy)butoxy]-4''-pyrrolidin-4-yl[1,1';3',1'']terphenyl-4-carboxylate

HRID 1261535Notes

Reaction equation

HRID 1261535 reaction equation
C(C1C=C(C2C=C(C3C=CC(C(OCC)=O)=CC=3)C=CC=2O)C=CC=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].BrCCCCO[Si](C(C)(C)C)(C)C.[C:53]([C:57]1[CH:58]=[C:59]([C:68]2[CH:69]=[C:70]([C:87]3[CH:92]=[CH:91][C:90]([C:93]([O:95][CH2:96][CH3:97])=[O:94])=[CH:89][CH:88]=3)[CH:71]=[CH:72][C:73]=2[O:74][CH2:75][CH2:76][CH2:77][CH2:78][O:79][Si:80]([C:83]([CH3:86])([CH3:85])[CH3:84])([CH3:82])[CH3:81])[CH:60]=[CH:61][C:62]=1N1CCCC1)([CH3:56])([CH3:55])[CH3:54]>>[C:53]([C:57]1[CH:58]=[C:59]([C:68]2[CH:69]=[C:70]([C:87]3[CH:88]=[CH:89][C:90]([C:93]([O:95][CH2:96][CH3:97])=[O:94])=[CH:91][CH:92]=3)[CH:71]=[CH:72][C:73]=2[O:74][CH2:75][CH2:76][CH2:77][CH2:78][O:79][Si:80]([C:83]([CH3:86])([CH3:84])[CH3:85])([CH3:81])[CH3:82])[CH:60]=[CH:61][C:62]=1[CH:14]1[CH2:15][NH:11][CH2:12][CH2:13]1)([CH3:54])([CH3:56])[CH3:55]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 582370(4-Bromobutoxy)(tert-butyl)dimethylsilaneHCID 66671790Ethyl 3''-tert-butyl-4'-hydroxy-4''-pyrrolidin-1-yl[1,1';3',1'']terphenyl-4-carboxylateHCID 66672253Ethyl 3''-tert-butyl-4'-[4-(tert-butyldimethylsilanyloxy)butoxy]-4''-pyrrolidin-1-yl[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 70815297Ethyl 3''-tert-butyl-4'-[4-(tert-butyldimethylsilanyloxy)butoxy]-4''-pyrrolidin-4-yl[1,1';3',1'']terphenyl-4-carboxylateYield 97%

Procedure

In a manner similar to that of Example 2a, by reacting 123 mg of ethyl 3″-tert-butyl-4′-hydroxy-4″-pyrrolidin-1-yl[1,1′;3′,1″]terphenyl-4-carboxylate (0.27 mmol) with 110 mg (0.34 mmol) of caesium carbonate and 80 μL of 1-bromo-4-(tert-butyldimethylsilanyloxy)butane (0.30 mmol), 170 mg of ethyl 3″-tert-butyl-4′-[4-(tert-butyldimethylsilanyloxy)butoxy]-4″-pyrrolidin-1-yl[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=97%) in the form of an oil.

Workup

  1. customare obtained (yield=97%) in the form of an oil

Sources & evidence

ORD record
ord-bb96008485004883a5904f1bb9ccab60
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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