Tetrahydrofuran → 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde

Temperature

-70 °C

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (2.0 g, 10 mmol) in anhydrous THF (50 mL) at −70° C. under nitrogen was added n-butyl lithium (2.5 M in hexane, 50 mmol) and the reaction mixture was stirred for 1 h at −70° C. The resulting orange gel was quenched with methyl formate (10 mL) and the reaction mixture was slowly warmed to RT. The mixture was poured into water (20 mL) and extracted with EtOAc (2×250 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated to afford 500 mg, (33%) of 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde as yellow solid. MS (ESI) m/z: 147.2 [M+1]+.

1. customThe resulting orange gel was quenched with methyl formate (10 mL)
2. temperaturethe reaction mixture was slowly warmed to RT
3. additionThe mixture was poured into water (20 mL)
4. extractionextracted with EtOAc (2×250 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-fe62e255054c4cf19f2615f2116869c1

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815877B2