Hydrochloric Acid → HCID 178437172, compound

Temperature

85 °C

4-Chloro-3-ethyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.76 g, 3.6 mmol) was suspended in n-PrOH (15 mL) then methylhydrazine (0.185 g, 4.01 mmol) was added. The mixture was heated at about 85° C. for about 20 min. The mixture was treated with concentrated aqueous HCl (0.330 mL, 4.01 mmol) then heated at about 110° C. for about 3.5 h. The solvent was evaporated under reduced pressure then the mixture was partitioned between water (20 mL) with aqueous HCl (5.0 N, 2 mL) and EtOAc (20 mL). The layers were separated then the aqueous layer was basified with saturated aqueous NaHCO3 and extracted with EtOAc (3×20 mL). The combined organics were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 8-ethyl-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.465 g, 64%): LC/MS (Table 2, Method a) Rt=1.83 min; MS m/z 201 (M+H)+.

1. temperaturethen heated at about 110° C. for about 3.5 h
2. customThe solvent was evaporated under reduced pressure
3. customthe mixture was partitioned between water (20 mL) with aqueous HCl (5.0 N, 2 mL) and EtOAc (20 mL)
4. customThe layers were separated
5. extractionextracted with EtOAc (3×20 mL)
6. dry with materialThe combined organics were dried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-16d211d98bed4f1a8a66a3577c19d657

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785639B2