Reaction #40476

Reaction equation

di-HCl

2-methyl nicotinic acid

6-chloro-7-fluoro-9H-β-carbolin-8-ylamine

EDCI

→

N-(6-chloro-7-fluoro-9H-β-carbolin-8-yl)-2-methyl-nicotinamide

Solvents

pyridine

Conditions

Workup

1. 1
   OtherThe pyridine was removed under reduced pressure
2. 2
   Otherthe resulting dark oil was triturated with saturated aqueous NaHCO3
3. 3
   OtherThe precipitate which formed
4. 4
   Filtrationwas filtered
5. 5
   Washwashed with MeOH
6. 6
   workup.ADDITIONThe material was treated with 2M HCl in Et2O
7. 7
   Otherto yield a gray solid

Procedure

A solution of 6-chloro-7-fluoro-9H-β-carbolin-8-ylamine (100 mg, 0.424 mmol) in pyridine (2.5 ml) was stirred at RT. 2-methyl nicotinic acid (70 mg, 0.509 mmol) was added, followed by EDCI (130 mg, 0.678 mmol). The suspension was stirred at 100° C. for a day. The pyridine was removed under reduced pressure and the resulting dark oil was triturated with saturated aqueous NaHCO3. The precipitate which formed was filtered and washed with MeOH. The material was treated with 2M HCl in Et2O to yield a gray solid, the di-HCl salt N-(6-chloro-7-fluoro-9H-β-carbolin-8-yl)-2-methyl-nicotinamide (110 mg).

Source