Reaction #2264762

Reaction equation

product

4,4-dimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

Intermediate 12

2-Chloro-3-(trifluoromethyl)benzoyl chloride

K2CO3

→

desired compound

Yield 48.8%

5-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-4,4-dimethyl-1-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

Yield 48.8%

Solvents

DCM

Conditions

Workup

1. 1
   OtherThe crude reaction mixture
2. 2
   Filtrationwas filtered
3. 3
   Concentrationconcentrated
4. 4
   Otherpurified on 12 g SiO2 column with 0-4% NH3/MeOH CH2Cl2

Procedure

To a solution of the product of Example 53, Step B (59 mg, 0.26 mmol) in DCM (2 mL) was added Intermediate 12 (63 mg, 0.26 mmol) and K2CO3 (89 mg, 0.65 mmol). The resulting suspension was stirred at room temperature for 2 h. The crude reaction mixture was filtered and concentrated and then purified on 12 g SiO2 column with 0-4% NH3/MeOH CH2Cl2 to give the desired compound (55 mg, 48%). MS (ESI): mass calcd. for C22H19ClF3N3O, 433.1. m/z found, 434.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.72 (dd, J=7.8, 1.4 Hz, 1H), 7.67 (s, 1H), 7.54-7.37 (m, 5H), 7.30 (dd, J=5.3, 3.3 Hz, 2H), 3.53-3.38 (m, 2H), 2.72-2.54 (m, 2H), 2.01 (d, J=6.3 Hz, 6H).

Source