6-BROMO-2-PYRIDINEMETHANAMINE

Application

The molecular structure of 6-bromo-2-pyridinemethylamine contains a bromine atom at position 6 and a methylamine functional group at position 2. Both positions are relatively easy sites for functional group transformation. The bromine atom in this substance can participate in a variety of coupling reactions, making it widely applicable in organic synthesis.

Synthesis

The general procedure for the synthesis of 6-bromo-2-pyridinemethanamine from the compound (CAS: 521917-57-7) is as follows: A214.1 (214.1 g) was suspended in anhydrous ethanol (420 mL) and heated at 70 °C for 30 min. To this non-homogeneous solution was slowly added hydrazine monohydrate. The reaction mixture became homogeneous within 1 min. Heating of the reaction mixture was continued for 3 hours, during which time the mixture gradually solidified to a white solid. Subsequently, 100 mL of ethanol was added to the reaction system and the mixture was filtered. The precipitate was washed well with ethanol and the filtrate was partially concentrated. The solid was collected by vacuum filtration. The filtrate was further concentrated to dryness and then ground with methanol. The product A214.2 was collected by vacuum filtration to give 14.3 g (93% yield) of white solid. The compound was analyzed by HPLC under the following conditions: retention time = 0.395 min (column: Chromolith SpeedROD 4.6 x 50 mm; run time: 4 min; mobile phase A: 10% methanol, 90% water with 0.1% trifluoroacetic acid; mobile phase B: 90% methanol, 10% water with 0.1% trifluoroacetic acid).LC/MS analysis showed [M+1]+ peaks of 187.12 and 189.12.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7006 - 7012
[2] Patent: WO2006/122137, 2006, A1. Location in patent: Page/Page column 158
[3] Organic Letters, 2013, vol. 15, # 9, p. 2290 - 2293
[4] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5046 - 5067