Reaktion #2032492

Reaktionsgleichung

TBAF

methyl 5-[(6-chloro-5-[6-fluoro-1-(2-hydroxyethyl)-1H-indol-5-yl]-1-{[2-(trimethylsilyl)-ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate

→

title compound

5-({6-chloro-5-[6-fluoro-1-(2-hydroxyethyl)-1H-indol-5-yl]-1 H-benzimidazol-2-yl}oxy)-2-methylbenzoic acid

Lösungsmittel

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeVolatiles were removed
2. 2
   workup.DISSOLUTIONthe residue was dissolved in MeOH (4 mL)
3. 3
   workup.ADDITIONtreated with 2.5 N aqueous NaOH (1.5 mL)
4. 4
   Sonstigeat rt
5. 5
   Sonstigeovernight
6. 6
   SonstigeReaction mixture
7. 7
   Waschenwashed with 1 M aqueous HCl and brine
8. 8
   TrocknenThe organic layer was dried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated

Vorschrift

TBAF (1 M in THF) (2 mL, 2 mmol) was added to a solution of methyl 5-[(6-chloro-5-[6-fluoro-1-(2-hydroxyethyl)-1H-indol-5-yl]-1-{[2-(trimethylsilyl)-ethoxy]methyl}-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate in THF (2 mL). The reaction was heated at 80° C. for 3 h. Volatiles were removed and the residue was dissolved in MeOH (4 mL) and treated with 2.5 N aqueous NaOH (1.5 mL). The reaction was stirred at 45° C. for 1 h, then at rt overnight. Reaction mixture was diluted with EtOAc and washed with 1 M aqueous HCl and brine. The organic layer was dried (Na2SO4), filtered, and concentrated. Chromatography over silica eluting with 8% MeOH/DCM afforded the title compound as a beige solid. 1H NMR (500 MHz, CD3OD): δ 7.86 (d, 1H), 7.48 (s, 1H), 7.44-7.37 (m, 3H), 7.33 (s, 1 H), 7.27 (d, 1H), 7.23 (d, 1H), 6.46 (d, 1H), 4.25 (t, 2H), 3.88 (t, 2H), 2.61 (s, 3H). LC-MS: m/e 480.2 (M+H)+ (1.79 min).

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