反応 #315012

反応方程式

azaindole N-oxide

DMF

Methanesulfonyl chloride

→

title compound

4-Chloro-1H-pyrrolo[2,3-b]pyridine

反応条件

後処理

1. 1
   温度The resulting mixture was heated at 68-77° C. until the reaction
2. 2
   温度The reaction was cooled to rt
3. 3
   その他quenched with water (10 mL)
4. 4
   温度The mixture was cooled to 5° C
5. 5
   workup.ADDITION10 N NaOH solution was added
6. 6
   温度to raise the pH of the solution to 7
7. 7
   温度The resulting slurry was warmed to rt
8. 8
   ろ過filtered
9. 9
   その他to collect the product
10. 10
    洗浄The product was washed with additional water
11. 11
    その他dried under vacuum
12. 12
    その他Rusty solid, 4-chloro-1H-pyrrolo[2,3-b]pyridine was collected

実験手順

The title compound was prepared according to the procedure described in WO2003082289A1. A solution of azaindole N-oxide (6.82 g, 51.0 mmol) in DMF (36.0 ml, 470 mmol) was heated to 50° C. Methanesulfonyl chloride (11.0 ml, 137 mmol) was added to the heated solution at such a rate as to maintain the reaction temperature at 65 to 75° C. The resulting mixture was heated at 68-77° C. until the reaction was judged complete by RPLC. The total reaction time was 4 hours. The reaction was cooled to rt and quenched with water (10 mL). The mixture was cooled to 5° C. 10 N NaOH solution was added to raise the pH of the solution to 7. The resulting slurry was warmed to rt, agitated for 1 h, and then filtered to collect the product. The product was washed with additional water and dried under vacuum. Rusty solid, 4-chloro-1H-pyrrolo[2,3-b]pyridine was collected. 1H NMR (Bruker, 400 MHz, DMSO-d6) 12.0 (br s, 1H), 8.19 (d, J=5.4 Hz, 1H), 7.60 (t, J=3.0 Hz, 1H), 7.20 (d, J=5.0 Hz, 1H), 6.52 (d, J=3.0 Hz, 1H).

出典