반응 #57230

반응 방정식

n-Butyllithium

diisopropylamine

N,N-dimethylformamide

4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

→

title compound

수율 66.0%

4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

수율 66.0%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The resulting reaction
2. 2
   workup.STIRRINGwas stirred at −78° C. for 2 h
3. 3
   workup.STIRRINGThe reaction was stirred at −78° C. for 2 h
4. 4
   기타quenched with saturated aqueous ammonium chloride solution (10 mL)
5. 5
   추출The mixture was extracted with ethyl acetate (2×20 mL)
6. 6
   건조the combined organic layers were dried over magnesium sulfate
7. 7
   농축concentrated in vacuo
8. 8
   기타Purification by silica gel chromatography (Analogix IF280, 70-100% CH2Cl2/hexanes)

실험 절차

n-Butyllithium (2.5M in hexanes, 3.56 mmol) was added dropwise to a solution of diisopropylamine (3.56 mmol) in anhydrous tetrahydrofuran (5 mL) at −78° C. under nitrogen. The reaction was stirred for 30 minutes at −78° C. and then a solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.97 mmol) in anhydrous tetrahydrofuran (1 mL) was added dropwise via syringe. The resulting reaction was stirred at −78° C. for 2 h and then a solution of N,N-dimethylformamide (11.88 mmol) in tetrahydrofuran (1 mL) was added dropwise by syringe. The reaction was stirred at −78° C. for 2 h and then quenched with saturated aqueous ammonium chloride solution (10 mL). The mixture was extracted with ethyl acetate (2×20 mL), and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography (Analogix IF280, 70-100% CH2Cl2/hexanes) afforded the title compound as a white solid (66%). ESMS [M+H]+: 365.0

출처