Lithium Hydroxide → [4-(4-Methoxy-4''-trifluoromethoxy-[1,1';3',1'']terphenyl-5'-ylmethoxy)-2-methyl-phenoxy]-acetic acid

HRID 19503

Reaktionsgleichung

Reaktionsgleichung von HRID 19503
Br[C:2]1[CH:3]=[C:4]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25]C)=[C:20]([CH3:27])[CH:19]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH:7]=1.[F:28][C:29]([F:41])([F:40])[O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.[C:42](=[O:45])([O-])[O-:43].[K+].[K+].[OH-].[Li+]>O1CCOCC1.C1(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)C=CC=CC=1.C(O)C.O>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:5]=[C:4]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:42]([OH:43])=[O:45])=[C:20]([CH3:27])[CH:19]=3)[CH:3]=[C:2]([C:34]3[CH:35]=[CH:36][C:31]([O:30][C:29]([F:41])([F:40])[F:28])=[CH:32][CH:33]=3)[CH:7]=2)=[CH:13][CH:12]=1

Komponenten

9

Edukt 4

HCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 691074205-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4'-methoxy-biphenyl

Produkt 1

HCID 11599107[4-(4-Methoxy-4''-trifluoromethoxy-[1,1';3',1'']terphenyl-5'-ylmethoxy)-2-methyl-phenoxy]-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178420554HCID 178420554, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5-Bromo-3-(4-ethoxy-3-methyl-phenoxymethyl)-4′-methoxy-biphenyl 15 (50 mg, 0.11 mmol) and 4-trifluoromethoxyphenylboronic acid (30 mg, 0.15 mmol, 1.3 equiv.) are dissolved in dioxane (0.5 mL). Potassium carbonate (38 mg, 0.27 mmol), water (0.05 mL) and ethanol (0.05 mL) are added, followed by tetrakis (triphenylphosphino)palladium (15.6 mg, 0.13 mmol). The mixture is stirred under nitrogen and subjected to microwave (170° C. for 10 min). Cooling, addition of 0.25 mL of aqueous 1N lithium hydroxide solution, and stirring for 3 hours at room temperature, followed by reversed-phase purification yielded [4-(4-methoxy-4″-trifluoromethoxy-[1,1′;3′,1″]terphenyl-5′-ylmethoxy)-2-methyl-phenoxy]-acetic acid A2. 1H-NMR (400 MHz, CDCl3) δ=7.50 (m, 3H), 7.42 (m, 4H), 7.17 (d, J=8.0 Hz, 2H), 6.87 (d, J=8.0 Hz, 2H), 6.75 (d, J=2.8 Hz, 1H), 6.65 (dd, J=8.8, 2.8 Hz, 1H), 6.58 (d, J=8.8 Hz, 1H), 5.17 (s, 2H), 4.50 (s, 2H), 3.73 (s, 3H), 2.16 (s, 3H). 19F-NMR (376 MHz, CDCl3) δ=−57.8. MS calculated for C30H26F3O6 (M+H+) 539.17. found 539.0.

Aufarbeitung

  1. custom(170° C. for 10 min)
  2. temperatureCooling
  3. stirringstirring for 3 hours at room temperature
  4. customfollowed by reversed-phase purification

Quellen und Nachweise

ORD-Eintrag
ord-23ddb7be655f4c35a298c86d3c047f61
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745445B2

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