반응 #587901

반응 방정식

trimethyl-prop-1-ynyl-silane

5-bromo-3-iodopyridin-2-amine

KOAc

LiCl

→

5-bromo-3-methyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine

용매

—

Petroleum ether

EtOAc

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타the mixture was degassed again
3. 3
   기타Excess DMF was removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in EtOAc (500 mL)
5. 5
   세척washed with saturated aqueous NaCl
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated
8. 8
   기타to give crude product, which
9. 9
   기타was purified via a silica gel column chromatography (100-200) (Petroleum ether

실험 절차

To a solution of 5-bromo-3-iodopyridin-2-amine (B-5-2) (30 g, 0.1 mol) in DMF (600 mL) were added KOAc (29.4 g, 0.3 mol) and LiCl (4.25 g, 0.1 mol). After the mixture was degassed under N2 for 3 times, Pd(OAc)2 (2.24 g, 0.01 mol) was added, and the mixture was degassed again. Then trimethyl-prop-1-ynyl-silane (56 g, 0.5 mol) was added. The resulting mixture was heated to 80-100° C. for 2 days. TLC (EtOAc: Petroleum ether=1:5) showed that the reaction was complete. Excess DMF was removed under reduced pressure. The residue was dissolved in EtOAc (500 mL), washed with saturated aqueous NaCl, dried over Na2SO4 and concentrated to give crude product, which was purified via a silica gel column chromatography (100-200) (Petroleum ether, then EtOAc:Petroleum ether=1:10) to give 5-bromo-3-methyl-2-(trimethylsilyl)-1H-pyrrolo[2,3-b]pyridine (B-5-3) (not pure, 5 g, 17.7%) as a brown oil.

출처