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

To a solution of 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (D22) (3.37 g, 9.99 mmol) in THF (50 mL) stirred at −35° C. was added 2M THF solution of LDA (9.99 mL, 19.99 mmol) and the mixture was stirred for 45 min at this temperature. Iodomethane (1.250 mL, 19.99 mmol) was added dropwise to the mixture and the mixture was then allowed to warm to RT over 2 hours. The reaction was quenched with addition of saturated NH4Cl aq. solution and the mixture was poured into saturated NH4Cl aq. solution (100 mL). The mixture was extracted with ethyl acetate. The organic layers were combined, washed with brine (100 mL), dried over MgSO4, filtered and evaporated in vacuo. The crude residue was purified by chromatography on silica, eluting with a gradient of 0-20% ethyl acetate in cyclohexane to give the title compound (2.93 g). LCMS (A): m/z (M+H)+ 351/353, C14H11BrN2O2S requires 350/352 (acidic).

1. customThe reaction was quenched with addition of saturated NH4Cl aq. solution
2. additionthe mixture was poured into saturated NH4Cl aq. solution (100 mL)
3. extractionThe mixture was extracted with ethyl acetate
4. washwashed with brine (100 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe crude residue was purified by chromatography on silica
9. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane

ORD record

ord-259ae8c09cf94737920a68f51ac6131e

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877742B2