Methylamine → 5-Bromo-N-methylpyridin-2-amine

Temperature

80 °C

A 20 ml microwave reaction vessel is charged with 2,5-Dibromo-pyridine (2.00 g, 8.44 mmol) and treated with methylamine (10.45 ml of a 33% solution in ethanol, 84.43 mmol) and warmed to 80° C. for 3 days. After this time the reaction is concentrated and the remaining solid is treated with 1M HCl (50 ml) and DCM. The layers are separated and the aqueous phase is basified using 1N NaOH (to pH˜11). The product was extracted into DCM (2×) and the combined organics were dried (MgSO4), filtered and concentrated to give the desired product I-96bis (1.20 g). 1H-NMR (400 MHz, DMSO-d6): 2.75 ppm (d, 3H), 6.44 ppm (d, 1H), 6.72 ppm (bs, 1H), 7.51 ppm (dd, 1H), 8.05 ppm (s, 1H)

1. concentrationAfter this time the reaction is concentrated
2. additionthe remaining solid is treated with 1M HCl (50 ml) and DCM
3. customThe layers are separated
4. extractionThe product was extracted into DCM (2×)
5. dry with materialthe combined organics were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-c14b74fcac3844a59b40c936305bb181

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09248187B2