Hydrochloric Acid → HCID 178437172, compound

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence