Reaktion #654515

Reaktionsgleichung

9-[(2,6-difluorophenyl)methyl]-4-hydroxy-5-carbamoyl carbazole

methyl bromoacetate

→

{9-[(2,6-difluorophenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester

Ausbeute 65.3%

Lösungsmittel

DMF

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe resultant white precipitate collected by filtration
2. 2
   Sonstigetriturated with diethyl ether/hexanes
3. 3
   Sonstigedried in vacuo

Vorschrift

40% Methanolic Triton B (0.49 mL, 1.07 mM) was added to a solution of the 9-[(2,6-difluorophenyl)methyl]-4-hydroxy-5-carbamoyl carbazole (290 mg, 0.82 mM) in 5 mL DMF at room temperature. After 15 minutes, methyl bromoacetate (259 mg, 1.65 mM) was added and the resultant mixture stirred at room temperature for 24 hours. The mixture was diluted with H2O and the resultant white precipitate collected by filtration, triturated with diethyl ether/hexanes, and dried in vacuo to afford 228 mg (65%) of the {9-[(2,6-difluorophenyl)methyl]-5-carbamoylcarbazol-4-yl}oxyacetic acid, methyl ester as a white solid. 1H NMR (CDCl3) δ 7.65 (d, 1H, J=8 Hz), 7.45-7.2 (m, 5H), 6.85 (t, 2H, J=8 Hz), 6.55 (d, 1H, J=8 Hz), 6.3 (br s, 1H), 6.0 (br s, 1H), 5.5 (s, 2H), 4.9 (s, 2H), and 3.8 (s, 3H). IR (KBr, cm−1) 3432, 3170, 1762, and 1675. MS (ES) m/e 425.

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