반응 #333251

반응 방정식

sodium chlorite

potassium dihydrogen phosphate

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

sulfamic acid

→

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

수율 98.1%

용매

water

1,4-dioxane

water

반응 조건

후처리

1. 1
   기타over ˜15 min
2. 2
   workup.ADDITIONAfter the addition
3. 3
   기타the ice bath was removed
4. 4
   workup.ADDITIONThe reaction mixture was diluted with water
5. 5
   추출extracted with EtOAc (3×)
6. 6
   세척The combined organic layers were washed with brine
7. 7
   건조then dried over MgSO4
8. 8
   농축concentrated

실험 절차

To a solution of 2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (226 mg, 0.51 mmol) in 1,4-dioxane (15 ml) and water (3 ml) at 0° C. was added sulfamic acid (297 mg, 3.06 mmol). Then a solution of sodium chlorite (80%, 75 mg, 0.66 mmol) and potassium dihydrogen phosphate (834 mg, 6.13 mmol) in water (12 ml) was added via dropping funnel over ˜15 min. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with brine then dried over MgSO4 and concentrated to afford 230 mg (98%) of 2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a light yellow powder.

출처