Reaktion #588385

Reaktionsgleichung

solution

methyl 2-(8-bromo-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate

Cs2CO3

5-formyl-2-furanboronic acid

→

methyl-2-{8-[5-(formyl)-2-furyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate

Ausbeute 46.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was thoroughly degassed
2. 2
   Sonstigewas removed under reduced pressure
3. 3
   SonstigeThe mixture was partitioned between ethyl acetate (100 mL) and water (15 mL)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent was removed under reduced pressure
8. 8
   Sonstigeto give crude residue, which
9. 9
   Sonstigewas purified by column chromatography

Vorschrift

To a solution of Example 33 (0.25 g, 0.64 mmol) in THF:H20 (4:1) were added Cs2CO3 (1.689 g, 5.16 mmol) and 5-formyl-2-furanboronic acid (0.180 g, 1.29 mmol). The reaction mixture was thoroughly degassed and freshly prepared tetrakis(triphenylphosphine)palladium(0) (0.186 g, 0.16 mmol) was added under nitrogen atmosphere at room temperature. The reaction mixture temperature was raised to 80° C. and continued stirring for 12 hr. The progress of the reaction was monitored by TLC analysis and upon completion of the reaction the THF was removed under reduced pressure. The mixture was partitioned between ethyl acetate (100 mL) and water (15 mL). The organic layer was separated, dried over Na2SO4 filtered and the solvent was removed under reduced pressure to give crude residue, which was purified by column chromatography using silica gel to give methyl-2-{8-[5-(formyl)-2-furyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl}pyrimidine-5-carboxylate (0.12 g, 46.2%)

Quelle