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

Temperature

70 °C

A solution of 2a (1.926 kg) in DMF (9.705 kg) was heated to about 50° C. Methanesulfonyl chloride (4.399 kg) 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 about 68 to 77° C. until the reaction was judged complete by reversed phase HPLC analysis. The reaction mixture was cooled to about 30° C., and then quenched with water (31.024 kg). Upon cooling the quenched reaction mixture to 5° C., sufficient 10 N NaOH solution was added to raise the pH of the solution to about 7. The resulting slurry was warmed to 25° C., agitated for approximately 1 h, and then filtered to collect the product. The product was washed with additional water, and dried under high vacuum at 45 to 50° C. to afford 1.904 kg of 3a.

1. temperatureThe resulting mixture was heated at about 68 to 77° C. until the reaction
2. temperatureThe reaction mixture was cooled to about 30° C.
3. customquenched with water (31.024 kg)
4. temperatureUpon cooling
5. customthe quenched reaction mixture to 5° C.
6. temperatureto raise the pH of the solution to about 7
7. temperatureThe resulting slurry was warmed to 25° C.
8. filtrationfiltered
9. customto collect the product
10. washThe product was washed with additional water
11. customdried under high vacuum at 45 to 50° C.

ORD record

ord-97467550d4534cf586ea19d465c04ae3

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105677B2