تفاعل #491454

معادلة التفاعل

DAST

1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol

→

desired product

المردود 5.5%

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

المردود 5.5%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةbefore being slowly warmed to 0° C. over 5 hours
2. 2
   أخرىThe reaction was quenched by addition of phosphate buffer (pH=8)
3. 3
   استخلاصextracted with DCM
4. 4
   استخلاصThe aqueous phase was extracted twice with 10 ml DCM
5. 5
   تجفيفThe combined organics were dried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe crude reaction material
9. 9
   أخرىwas purified by flash chromatography on SiO2 (20% EtOAc/hexanes/0.2% TEA)
10. 10
    workup.ADDITIONFractions containing the
11. 11
    أخرىwere further purified with 40% EtOAc/hexanes (+0.1% TEA)

الإجراء التجريبي

DAST [(Et2NSF3) 0.12 ml, 0.916 mmol] was added dropwise to a solution of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (0.102 g, 0.203 mmol) in 6.0 ml of anhydrous DCM at −78° C. The reaction was stirred at −78° C. for one hour before being slowly warmed to 0° C. over 5 hours. The reaction was quenched by addition of phosphate buffer (pH=8) and extracted with DCM. The aqueous phase was extracted twice with 10 ml DCM. The combined organics were dried over Na2SO4, filtered and concentrated. The crude reaction material was purified by flash chromatography on SiO2 (20% EtOAc/hexanes/0.2% TEA). Fractions containing the desired fluorinated product were further purified with 40% EtOAc/hexanes (+0.1% TEA). Isolated 5.7 mg desired product.

المصدر