Sodium Carbonate → 3′-[2-(Dimethylamino)ethoxy][1,1′-biphenyl]-4-carboxylic acid

HRID 1264309Notes

Reaction equation

[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8](I)[CH:9]=[CH:10][CH:11]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([OH:16])=[O:15].C(=O)([O-])[O-].[Na+].[Na+].C(C#N)(C)=O>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.O>[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:20]2[CH:21]=[CH:22][C:17]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Stirred a solution of 3-(2-Dimethylaminoethoxy)phenyl iodide (0.495 g, 1.70 mmoles), 4-carboxybenzeneboronic acid (Lancaster, 0.282 g, 1.70 mmoles), and sodium carbonate (0.360 g, 3.40 mmoles) in 1:1 H2O: AcCN (20 mL) under vacuum for five minutes, followed by the addition of tetrakis(triphenylphosphine)palladium (0) (0.170g). The reaction mixture was heated (90° C.) for three hours, and the catalyst was filtered off through Celite. The effluent was concentrated slightly to remove the AcCN, and the resulting aqueous solution was acidified with 2N HCl and purified on an HPLC to yield 0.462 g of the title compound as the TFA salt. MS (ion spray) m/z 286 (M+H)+.

Workup

filtrationthe catalyst was filtered off through Celite
concentrationThe effluent was concentrated slightly
customto remove the AcCN
custompurified on an HPLC

Sources & evidence

ORD record: ord-938a08a83dd946319d0d8234711f0a87
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06541505B1

Reaction notes

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