Pyridine → 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid pentafluorophenyl ester

HRID 1062259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062259
[Br:1][C:2]1[C:3]([F:21])=[C:4]([F:20])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[CH3:19])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N1C=CC=CC=1.FC(F)(F)C(O[C:33]1[C:38]([F:39])=[C:37]([F:40])[C:36]([F:41])=[C:35]([F:42])[C:34]=1[F:43])=O>CN(C)C=O.CCOCC>[F:39][C:38]1[C:33]([O:8][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Br:1])[C:3]([F:21])=[C:4]([F:20])[C:5]=2[NH:11][C:12]2[CH:17]=[CH:16][C:15]([I:18])=[CH:14][C:13]=2[CH3:19])=[C:34]([F:43])[C:35]([F:42])=[C:36]([F:41])[C:37]=1[F:40]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 98907755-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid

Produkt 1

HCID 233984895-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid pentafluorophenyl esterAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid (prepared as described in WO 99/01426) (1.61 g, 3.4 mmol) and pyridine (0.31 mL, 3.83 mmol) in anhydrous dimethylformamide (7 mL) was added 10 pentafluorophenyl trifluoroacetate (0.71 mL, 4.13 mmol). The resultant solution was stirred at ambient temperature for 18 h. The reaction mixture was diluted with ether (100 mL) and washed with water (40 mL), 0.1 M aqueous hydrochloric acid (40 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated brine (40 mL). The organics were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a foam that was purified on silica gel. Elution with hexanes-ethyl acetate (19:1) afforded 5-Bromo-3,4-difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid pentafluorophenyl ester (1.95 g, 89%) as a pale-yellow powder: 1H NMR (400 MHz, CDCl3) δ 8.59 (s, 1H), 8.24 (d, J=5.8 Hz, 1H), 7.54 (s, 1H), 7.45 (d, J=8.4 Hz, 1H), 6.70 (dd, J=8.4, 5.3 Hz, 1H), 2.26 (s, 3H).

Aufarbeitung

  1. washwashed with water (40 mL), 0.1 M aqueous hydrochloric acid (40 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated brine (40 mL)
  2. dry with materialThe organics were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a foam that
  5. customwas purified on silica gel
  6. washElution with hexanes-ethyl acetate (19:1)

Quellen und Nachweise

ORD-Eintrag
ord-1cb45f89bd84436cad43987b518ce92c
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960614B2

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