반응 #333250

반응 방정식

iodomethane

2-(4,6-difluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

sodium hydride

→

2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

수율 24.3%

용매

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at 0° C. for 30 min
2. 2
   workup.WAITat room temperature for 30 min
3. 3
   기타The reaction was quenched with sat'd NH4Cl
4. 4
   workup.ADDITIONdiluted with water
5. 5
   추출extracted with EtOAc (2×)
6. 6
   세척The combined organics were washed with sat LiCl and brine
7. 7
   건조then dried over MgSO4
8. 8
   농축concentrated
9. 9
   기타The crude residue was purified by silica gel chromatography with 20% to 100% EtOAc/heptane

실험 절차

To a solution of 2-(4,6-difluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (890 mg, 2.1 mmol) in DMF (9 ml) at 0° C. was added sodium hydride (60% in mineral oil, 279 mg, 2.49 mmol). The reaction mixture was stirred at 0° C. for 10 min then iodomethane (0.18 ml, 2.9 mmol) was slowly added. The mixture was stirred at 0° C. for 30 min then at room temperature for 30 min. The reaction was quenched with sat'd NH4Cl, diluted with water and extracted with EtOAc (2×). The combined organics were washed with sat LiCl and brine then dried over MgSO4 and concentrated. The crude residue was purified by silica gel chromatography with 20% to 100% EtOAc/heptane to provide 226 mg (22%) of 2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a yellow solid.

출처