Iodoethane → HCID 59620027, compound

Temperature

-78 °C

To a solution of 3-amino-5-bromopyridine (CAS#13535-01-8, 520 mg, 3.0 mmol) in THF (12 mL) at −78° C. was added potassium bis(trimethylsilyl)amide (0.5 M in toluene, 6.9 mL, 3.45 mmol). The reaction was stirred for 20 minutes at −78° C. and was then charged with iodoethane (0.25 mL, 3.15 mmol). The reaction was stiffed for an additional 30 minutes, at which time mixture was charged with additional potassium bis(trimethylsilyl)amide (0.5 M in toluene, 6.9 mL, 3.45 mmol) and iodoethane (0.25 mL, 3.15 mmol). The reaction was then permitted to warm to −20° C. over 2 h at which time it was quenched with aqueous ammonium hydroxide (5 mL) and was stirred for 30 minutes at room temperature. The reaction was then diluted with brine and ethyl acetate. The layers were separated and the aqueous layer was extracted two additional times. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford both (5-bromo-pyridin-3-yl)-ethyl-amine and (5-bromo-pyridin-3-yl)-diethyl-amine separately.

1. waitThe reaction was stiffed for an additional 30 minutes, at which time mixture
2. temperatureto warm to −20° C. over 2 h at which time it
3. customwas quenched with aqueous ammonium hydroxide (5 mL)
4. stirringwas stirred for 30 minutes at room temperature
5. additionThe reaction was then diluted with brine and ethyl acetate
6. customThe layers were separated
7. extractionthe aqueous layer was extracted two additional times
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%)

ORD record

ord-f2dca4b88eaf4192b85e86e380d9f258

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778972B2