Reaktion #90455

Reaktionsgleichung

N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide

lithium hydroxide

dimethylformamide

mercaptoacetic acid

→

N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-3-methoxyaniline

Ausbeute 88.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed sequentially with water, saturated sodium bicarbonate solution, water (3×) and brine
2. 2
   TrocknenThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Sonstigecondensed
5. 5
   SonstigeThe crude reaction mixture
6. 6
   Sonstigewas purified in 30% EtOAc/hexanes (+0.2% TEA), with 13.6 mg
7. 7
   Sonstigeisolated

Vorschrift

To a vial containing N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-N-(3-methoxyphenyl)-4-nitrobenzenesulfonamide (21.0 mg, 0.030 mmol; see representative procedure 4) was added lithium hydroxide (3.2 mg, 0.134 mmol), dimethylformamide (0.5 ml, 0.06 M) and mercaptoacetic acid (4.2 ul 0.060 mmol). After stirring at rt for 1 h the reaction mixture was diluted with EtOAc and washed sequentially with water, saturated sodium bicarbonate solution, water (3×) and brine. The organic layer was dried over Na2SO4, filtered and condensed. The crude reaction mixture was purified in 30% EtOAc/hexanes (+0.2% TEA), with 13.6 mg isolated. Yield=88%

Quelle