Acetic Acid → (5-Bromo-2-iodo-benzyl)-ethyl-amine

To 5-bromo-2-iodo-benzaldehyde (5.0 g, 16.1 mmol) in methanol (20 mL) was added ethylamine (2M in methanol; 16 mL, 24.0 mmol), followed by acetic acid (1.0 mL, 17.8 mmol), and the mixture was stirred at room temperature for 30 minutes. Sodium cyanoborohydride (2.0 g, 31.8 mmol) was then added over 5 minutes, and the reaction was stirred at room temperature over the weekend. The mixture was concentrated and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% methanol in dichloromethane) to give the title compound.

1. stirringthe reaction was stirred at room temperature over the weekend
2. concentrationThe mixture was concentrated
3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
4. extractionThe aqueous layer was extracted with ethyl acetate
5. dry with materialthe combined organic layers were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography (0-5% methanol in dichloromethane)

ORD record

ord-096e142eb4c94005bdc8aaae818bb679

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785393B2