Potassium Carbonate → Ethyl 3''-tert-butyl-4-hydroxy-4''-pyrrolidin-1-yl[1,1';3',1'']terphenyl-4-carboxylate

HRID 1158169Notes

Reaction equation

HRID 1158169 reaction equation
BrC1C=C(C2C=CC(C(OCC)=O)=CC=2)C=CC=1[OH:8].C(C1C=C(B(O)O)C=CC=1N1CCCC1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[C:44]([C:48]1[CH:49]=[C:50]([C:59]2[CH:60]=[C:61]([C:66]3[CH:71]=[CH:70][C:69]([C:72]([O:74][CH2:75][CH3:76])=[O:73])=[CH:68][CH:67]=3)[CH:62]=[CH:63][C:64]=2O)[CH:51]=[CH:52][C:53]=1[N:54]1[CH2:58][CH2:57][CH2:56][CH2:55]1)([CH3:47])([CH3:46])[CH3:45]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:44]([C:48]1[CH:49]=[C:50]([C:59]2[CH:60]=[C:61]([C:66]3[CH:71]=[CH:70][C:69]([OH:8])([C:72]([O:74][CH2:75][CH3:76])=[O:73])[CH2:68][CH:67]=3)[CH:62]=[CH:63][CH:64]=2)[CH:51]=[CH:52][C:53]=1[N:54]1[CH2:58][CH2:57][CH2:56][CH2:55]1)([CH3:45])([CH3:46])[CH3:47]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 16657517Ethyl 3'-bromo-4'-hydroxybiphenyl-4-carboxylateHCID 66671790Ethyl 3''-tert-butyl-4'-hydroxy-4''-pyrrolidin-1-yl[1,1';3',1'']terphenyl-4-carboxylateHCID 66672251(3-(Tert-butyl)-4-(pyrrolidin-1-yl)phenyl)boronic acid

Product 1

HCID 86617898Ethyl 3''-tert-butyl-4-hydroxy-4''-pyrrolidin-1-yl[1,1';3',1'']terphenyl-4-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a manner similar to that of Example 1d, by reacting 1 g of ethyl 3′-bromo-4′-hydroxy-biphenyl-4-carboxylate (3 mmol) with 1.2 g of 3-tert-butyl-4-pyrrolidinophenylboronic acid (4.5 mmol) in the presence of 5 mL of 2M potassium carbonate (10 mmol) and 360 mg of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), 900 mg of ethyl 3″-tert-butyl-4′-hydroxy-4″-pyrrolidin-1-yl[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=63%) in the form of a yellow solid.

Workup

  1. customare obtained (yield=63%) in the form of a yellow solid

Sources & evidence

ORD record
ord-24edd09aec4247748ee84274ead5f41f
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

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