Oxalyl chloride → 4-Chloro-1-methyl-7-(1-piperidinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine

Temperature

0 °C

A solution of oxalylchloride (3.43 ml) in DCM (40 ml) was cooled to 0° C. and 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (3.75 g) was added portionwise followed by the addition of DMF (4 drops). The reaction mixture was stirred at 0° C. for 90 min, DCM (5 ml) was added and stirring continued for a further 30 min. The reaction mixture was evaporated and the residue dissolved in dichloromethane (20 ml) and dimethylformamide (10 ml). N-ethylmorpholine (9.09 ml) followed by piperidine (3.53 ml) were added and the mixture stirred at 0° C. for 45 min. The reaction mixture was evaporated and the residue dissolved in EtOAc (150 ml). The organic layer washed with water (100 ml), sodium bicarbonate (3×100 ml) and brine (30 ml) then dried (MgSO4) and evaporated to a yellow oil. The oil was triturated with diethyl ether, and the solid filtered and dried at 60° C. under vacuum, to afford the title compound (3.95 g).

1. stirringstirring
2. waitcontinued for a further 30 min
3. customThe reaction mixture was evaporated
4. dissolutionthe residue dissolved in dichloromethane (20 ml)
5. additionwere added
6. stirringthe mixture stirred at 0° C. for 45 min
7. customThe reaction mixture was evaporated
8. dissolutionthe residue dissolved in EtOAc (150 ml)
9. washThe organic layer washed with water (100 ml), sodium bicarbonate (3×100 ml) and brine (30 ml)
10. dry with materialthen dried (MgSO4)
11. customevaporated to a yellow oil
12. customThe oil was triturated with diethyl ether
13. filtrationthe solid filtered
14. customdried at 60° C. under vacuum

ORD record

ord-279374d425db4ec4a2bab99f1988d9e0

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589206B2