Acetic Acid → 4-((1-benzylpiperidin-3-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine

A mixture of (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone (1.45 g, 2.84 mmol), anhydrous hydrazine (0.273 g, 8.53 mmol) and AcOH (0.163 mL, 2.84 mmol) was heated in EtOH (35 mL) at reflux for about 16 h. The reaction mixture was cooled to room temperature, the solvent was removed under reduced pressure and the residue partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (60 mL). The organic phase was washed with brine (40 mL) and concentrated to yield 4-((1-benzylpiperidin-3-yl)(hydrazono)methyl)-5-chloro-1H-pyrrolo[2,3-b]pyridine (1.04 g, quantitative) as a brown amorphous solid that was used directly in the next step without further purification: LC/MS (Table 2, Method a) Rt=1.57 min; MS m/z: 368 (M+H)+.

1. temperatureat reflux for about 16 h
2. customthe solvent was removed under reduced pressure
3. customthe residue partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (60 mL)
4. washThe organic phase was washed with brine (40 mL)
5. concentrationconcentrated

ORD record

ord-a5fca0d3e20a4948a545a390fec71a1a

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365579B2