Dimethylformamide → 4-Bromo-1-phenylsulfonyl-7-azaindole-2-carboxyaldehyde

Temperature

-78 °C

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

1. customThe resulting reaction
2. stirringwas stirred at −78° C. for 2 h
3. stirringThe reaction was stirred at −78° C. for 2 h
4. customquenched with saturated aqueous ammonium chloride solution (10 mL)
5. extractionThe mixture was extracted with ethyl acetate (2×20 mL)
6. dry with materialthe combined organic layers were dried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customPurification by silica gel chromatography (Analogix IF280, 70-100% CH2Cl2/hexanes)

ORD record

ord-442fc6c7799c4a1b851161ffd36bf44e

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07419988B2