Ammonium Hydroxide → 3-(Difluoromethoxy)pyridin-2-amine

Temperature

100 °C

To a steel bomb were charged with 2-methoxyethanol (20 ml), 2-bromo-3-(difluoromethoxy)pyridine (1.95 g, 8.7 mmol), conc. aqueous NH4OH (28-30%, 5 ml, 79 mmol) and Cu2O (0.25 g, 1.7 mmol). The reaction mixture was heated at 100° C. for 23 h, then cooled to 0° C., and partitioned between mixture of EtOAc/aq. 3 N NaOH/H2O (40 ml/10 ml/30 ml). The organic phase layer was collected, washed with saturated aqueous NaHCO3 solution (30 ml), brine (40 ml), dried (Na2SO4), and concentrated to produce 1.12 g of 3-(difluoromethoxy)pyridin-2-amine which was carried forward without further purification:

1. temperaturecooled to 0° C.
2. custompartitioned between mixture of EtOAc/aq
3. customThe organic phase layer was collected
4. washwashed with saturated aqueous NaHCO3 solution (30 ml), brine (40 ml)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated

ORD record

ord-9a0c5ff925da4d5b88d86fab2fc54d5f

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865732B2