Acetic Anhydride → HCID 57950447, compound

Temperature

80 °C

4-(Imidazo[1,2-a]pyridin-6-ylmethoxy)pyridine 1-oxide (1.69 g, 7.04 mmol) was heated at 140° C. in acetic anhydride (20 mL) for 4 h. The mixture was concentrated and heated at 80° C. for 3 h in a mixture of 1:1 MeOH/H2O (50 mL). The resulting solution was concentrated. The residue was partially dissolved in iPrOH (75 mL). Et2O (200 mL) was added, and the mixture was allowed to sit at ambient temperature for 1 h. The resulting solids were collected by filtration, washed with Et2O and dried under reduced pressure. The solids were again subjected to iPrOH and Et2O, and the solids were removed by filtration. The filtrate was concentrated to afford the title compound (0.47 g, 28%) as a dark brown solid: 1H NMR (300 MHz, CD3OD) δ 8.60 (d, J=0.7 Hz, 1H), 7.87 (d, J=0.6 Hz, 1H), 7.59 (d, J=1.4 Hz, 1H), 7.57 (s, 1H), 7.40-7.27 (m, 2H), 6.18 (dd, J=7.3, 2.5 Hz, 1H), 6.05 (d, J=2.5 Hz, 1H), 5.13 (s, 2H).

1. concentrationThe mixture was concentrated
2. concentrationThe resulting solution was concentrated
3. dissolutionThe residue was partially dissolved in iPrOH (75 mL)
4. additionEt2O (200 mL) was added
5. filtrationThe resulting solids were collected by filtration
6. washwashed with Et2O
7. customdried under reduced pressure
8. customthe solids were removed by filtration
9. concentrationThe filtrate was concentrated

ORD record

ord-a0f4733a1db2455abc5a65795e3f4918

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716308B2