4-Diethylamino-3-ethylphenylboronic acid → Ethyl 4'-[3-(tert-butyldimethylsilanyloxy)propoxy]-4''-diethylamino-3''-ethyl[1,1';3',1'']terphenyl-4-carboxylate

HRID 1261528Notes

Reaction equation

HRID 1261528 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[CH2:31]([N:33]([CH2:45][CH3:46])[C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][C:35]=1[CH2:43][CH3:44])[CH3:32]>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>[Si:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=2)=[CH:3][C:2]=1[C:37]1[CH:38]=[CH:39][C:34]([N:33]([CH2:45][CH3:46])[CH2:31][CH3:32])=[C:35]([CH2:43][CH3:44])[CH:36]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 666717804-Diethylamino-3-ethylphenylboronic acidHCID 66671827Ethyl 3'-bromo-4'-[3-(tert-butyldimethylsilanyloxy)propoxy]biphenyl-4-carboxylate

Product 1

HCID 66672171Ethyl 4'-[3-(tert-butyldimethylsilanyloxy)propoxy]-4''-diethylamino-3''-ethyl[1,1';3',1'']terphenyl-4-carboxylateYield 39.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a manner similar to that of Example 1d, by reacting 1.4 g (2.9 mmol) of ethyl 3′-bromo-4′-[3-(tert-butyldimethylsilanyloxy)propoxy]biphenyl-4-carboxylate (obtained in Example 5b) with 900 mg of 4-diethylamino-3-ethylphenylboronic acid (4 mmol) in the presence of tetrakis(triphenylphosphine)palladium, 674 mg of ethyl 4′-[3-(tert-butyldimethylsilanyloxy)propoxy]-4″-diethylamino-3″-ethyl[1,1′;3′,1″]terphenyl-4-carboxylate (yield=39%) are obtained in the form of a colorless oil.

Sources & evidence

ORD record
ord-312c5bdd29144f8587d0170f468b0c79
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

Loading…