Methyl iodide → 1-(Phensulfonyl)-5-chloro-2-methyl-1H-pyrrolo[3,2-B]pyridine

Temperature

0 °C

1.6 M n-butyllithium in hexanes (24 mL, 39 mmol) was added to a solution of N,N-diisopropylamine (5.8 mL, 42 mmol) in THF (80 mL) at −78° C. Following complete addition, the mixture was allowed to stir at 0° C. for 30 minutes and was then re-cooled to −78° C. A solution of 5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridine (7.6 g, 26 mmol, from Step 1) in THF (38 mL) was added dropwise. After stirring at −78° C. for 1 hour, methyl iodide (3.2 mL, 52 mmol) was added. The mixture was allowed to slowly reach room temperature, at which time it was quenched by the addition of saturated NH4Cl. The product was extracted with EtOAc, and the extracts were washed with water (2×), brine, dried over sodium sulfate, filtered and concentrated to afford product as a yellow oil which was used without further purification (8.0 g, 100%).

1. additionaddition
2. temperaturewas then re-cooled to −78° C
3. stirringAfter stirring at −78° C. for 1 hour
4. customwas allowed to slowly reach room temperature, at which time it
5. customwas quenched by the addition of saturated NH4Cl
6. extractionThe product was extracted with EtOAc
7. washthe extracts were washed with water (2×), brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customto afford product as a yellow oil which
12. customwas used without further purification (8.0 g, 100%)

ORD record

ord-db82d31090d44eee80b1a0029f74aae8

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309246B2