Methyl iodide → 4-Bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Temperature

-50 °C

To a stirring solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (20.08 g) in anhydrous Tetrahydrofuran (200 ml) at −50° C. was added LDA (66.2 ml) dropwise over 20 min. The resulting suspension was stirred at −50° C. for 1 h then methyl iodide (22.34 ml) was added dropwise over 20 min. The reaction mixture was stirred at −30° C. for 1 h then quenched by the addition of water. The layers were separated and the aq was re-extracted with DCM. The THF layer was concentrated in vacuo then re-dissolved in DCM. The DCM extracts were then combined and washed with water, brine, then dried over magnesium sulfate, filtered and evaporated to yield an oily residue that was recrystallised using cyclohexane:ethyl acetate (5:1) to yield a solid which was triturated using methanol, collected by filtration then dried in vacuo at 45° C. overnight to yield the title compound, 10.52 g as a pale yellow solid.

1. stirringThe reaction mixture was stirred at −30° C. for 1 h
2. customthen quenched by the addition of water
3. customThe layers were separated
4. extractionthe aq was re-extracted with DCM
5. concentrationThe THF layer was concentrated in vacuo
6. dissolutionthen re-dissolved in DCM
7. washwashed with water, brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customevaporated
11. customto yield an oily residue that
12. customwas recrystallised
13. customto yield a solid which
14. customwas triturated
15. filtrationcollected by filtration
16. customthen dried in vacuo at 45° C. overnight

ORD record

ord-88c3a4a8656e457c84232339316ccfb3

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326987B2