Sodium Carbonate → N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide

HRID 68617

Reaktionsgleichung

Reaktionsgleichung von HRID 68617
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][N:14]([CH3:25])[S:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2Br)=[CH:5][CH:4]=1.[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][O:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][N:14]([CH3:25])[S:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][C:10]=2[C:37]2[CH:36]=[CH:35][CH:34]=[C:33]([C:32]([F:43])([F:42])[F:31])[CH:38]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 66869194N-(4-(4-methoxybenzyloxy)-3-bromobenzyl)-4-fluoro-N-methylbenzenesulfonamide

Produkt 1

HCID 66868532N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamideAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of bromide 34 (1.0 g, 2.02 mmol, 1 eq) and 3-(trifluoromethyl)phenyl boronic acid (575 mg, 3.03 mmol, 1.5 eq, Aldrich, Milwaukee, Wis., USA) in dimethoxyethane (70 mL), was added sodium carbonate solution (9 mL of a 2 M solution) and tetrakis-triphenylphosphine palladium (233 mg, 0.1 eq). The mixture was stirred at 90° C. for 16 h, cooled to room temperature, and concentrated in vacuo. The resultant residue was partitioned between EtOAc and saturated sodium bicarbonate solution, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography (0-40% EtOAc/hexane) to give 790 mg (72%) of N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide (35). 1HNMR (CD3OD, 400 MHz): δ 7.84 (m, 3H), 7.65 (d, 1H), 7.44-7.54 (m, 3H), 7.18-7.30 (m, 5H), 7.04 (d, 1H), 6.85 (d, 2H), 5.02 (s, 2H), 4.14 (s, 2H), 3.80 (s, 3H), 2.63 (s, 3H). MS (ESI): MH+=560.1. HPLC (Method B) tR=4.57 min.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue was partitioned between EtOAc and saturated sodium bicarbonate solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography (0-40% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6e89b36e6e7e4c7abb77e0bd3136f910
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822467B2

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