Propargyl bromide → 3-(Prop-2-ynyloxy)pyridine

To a mixture of 3-hydroxypyridine (5.0 g, 52 mmol) and potassium hydroxide (8.8 g, 158 mmol) in N,N-dimethylformamide (30 mL) was added propargyl bromide (7.5 g, 63 mmol) dropwise at about 5-10 C and the mixture was stirred at room temperature for about 15 min. The reaction was quenched by addition of water and the product was extracted with dichloromethane. The combined organic extracts were washed with water and then stirred with activated charcoal for 30 min. The mixture was filtered through Celite and the filtrate was concentrated under vacuum to provide Example 638. 1H NMR (300 MHz, CDCl3): δ 2.57 (t, J=3.0 Hz, 1H), 4.77 (d, J=3.0 Hz, 2H), 7.30 (m, 2H), 8.27 (dd, J=3.0, 7.6 Hz, 1H), 8.40 (d, J=3.0 Hz, 1H).

1. customThe reaction was quenched by addition of water
2. extractionthe product was extracted with dichloromethane
3. washThe combined organic extracts were washed with water
4. stirringstirred with activated charcoal for 30 min
5. filtrationThe mixture was filtered through Celite
6. concentrationthe filtrate was concentrated under vacuum
7. customto provide Example 638

ORD record

ord-21dc6c9bd970425c8680c3339b511d13

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468371B2