Hydrochloric Acid → HCID 22477256, compound

Temperature

-75 °C

A solution of lithium diisopropylamine {prepared by treating a solution of diisopropylamine (33.6 mL) in tetrahydrofuran (250 mL) with butyl lithium in hexanes (70.4 mL, 2.5M) at −35° C., at −75° C., was treated dropwise with a solution of 1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [40 g, Reference Example 9(a)] in dry tetrahydrofuran (250 mL) at −75° C. whilst maintaining the reaction temperature below −60° C. After stirring at −75° C. for 3 hours the reaction mixture was allowed to warm to 5° C. over 2 hours then recooled to −75° C. and then treated with dimethylformamide (62 mL). The reaction mixture was left to warm to room temperature over 1 hour then poured into hydrochloric acid (800 mL, 1%) and then evaporated to remove the tetrahydrofuran. The resulting suspension was filtered and the solid was washed with water, then dried and then was subjected to flash column chromatography on silica eluting with dichloromethane to give the title compound (24.37 g) as a white solid.

1. temperaturewhilst maintaining the reaction temperature below −60° C
2. temperatureto warm to 5° C. over 2 hours
3. customthen recooled to −75° C.
4. waitThe reaction mixture was left
5. temperatureto warm to room temperature over 1 hour
6. customevaporated
7. customto remove the tetrahydrofuran
8. filtrationThe resulting suspension was filtered
9. washthe solid was washed with water
10. customdried

ORD record

ord-6bc679f349fd4b1c86e5c0ba3a1c2aea

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943616B2