Reaction #314297

Reaction equation

trifluoroacetamide

3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

sodium hydride

N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide

→

1-(6-Amino-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Solvents

methanol

diethylamine

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherovernight
2. 2
   Otherat 45° C
3. 3
   FiltrationThe product was filtered off
4. 4
   Washwashed with a small amount of DCM

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 127 mg (0.46 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one, 22 mg (0.55 mmol) of 60% sodium hydride, 155 mg (0.55 mmol) of N-(6-bromomethyl-pyridin-2-yl)-2,2,2-trifluoro-acetamide and 1 mL of N,N-dimethylformamide. The 130 mg of trifluoroacetamide product were heated to 60° C. in a mixture of 1 mL of methanol and 4 mL of diethylamine for 3 h, then overnight at 45° C. The product was filtered off and washed with a small amount of DCM. Yield: 36 mg of a white solid: LC-MSD, m/z for C23H20N4O2 [M+H]+=385.2; HPLC retention time: 0.8 min.

Source