Reaction #160410

Reaction equation

N-[(2-Trifluoromethyl-7-bromo-1H-indol-5-yl)methyl]-5-(trifluoromethyl)-2-pyridinecarboxamide

Intermediate 6

N-[(2-Trifluoromethyl-7-bromo-1H-indol-5-yl)methyl]-5-(trifluoromethyl)-2-pyridinecarboxamide

2-tri-n-butylstannyl pyridine

lithium chloride

→

title compound

N-{[7-(2-pyridinyl)-2-(trifluoromethyl)-1H-indol-5-yl]methyl}-6-(trifluoromethyl)-3-pyridinecarboxamide

Solvents

Toluene

Conditions

Workup

1. 1
   Otherde-gassed
2. 2
   workup.ADDITIONThe reaction mixture was poured into water (20 mL)
3. 3
   Extractionextracted with ethyl acetate (40 mL)
4. 4
   ExtractionThe organic extract
5. 5
   Washwas then washed with water (2×20 mL)
6. 6
   Dryingdried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Otherthe solvent removed
9. 9
   OtherThe resulting residues were purified by MDAP
10. 10
    Otherevaporated to dryness

Procedure

In a 2 mL microwave reactor vial N-[(2-Trifluoromethyl-7-bromo-1H-indol-5-yl)methyl]-5-(trifluoromethyl)-2-pyridinecarboxamide (Intermediate 6, 50 mg), 2-tri-n-butylstannyl pyridine (Frontier Scientific Inc., 79 mg), lithium chloride (45.5 mg), copper(I) iodide (2.04 mg) and tetrakis(triphenylphosphine)palladium(0) (12.39 mg) were stirred in Toluene (2 mL) and de-gassed using argon gas. The reaction mixture was then heated in a microwave reactor at 140° C. for 3 h. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (40 mL). The organic extract was then washed with water (2×20 mL), dried (MgSO4), filtered and the solvent removed. The resulting residues were purified by MDAP and evaporated to dryness to give the title compound as an off white solid (25.7 mg);

Source