Réaction #90421

Équation de réaction

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

Rendement 88.0%

Solvants

EtOAc

Conditions de réaction

Traitement

1. 1
   Lavagewashed sequentially with water, saturated sodium bicarbonate solution, water (3×) and brine
2. 2
   SéchageThe organic layer was dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Autrecondensed
5. 5
   AutreThe crude reaction mixture
6. 6
   Autrewas purified in 30% EtOAc/hexanes (+0.2% TEA), with 13.6 mg
7. 7
   Autreisolated

Mode opératoire

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%

Source