Calcium Carbonate → HCID 89996153, compound

To a stirred solution of 5-bromo-3-bromomethyl-2-iodo-pyridine (25.0 g, crude, 66.313 mmol, 1 eq) in 1,4-dioxane (200 mL) was added suspension of CaCO3 (34.5 mL, 345 mmol, 5.2 eq) in water (200 mL) at room temperature. Resulting reaction mixture was refluxed for 10 hours. After complete consumption of starting material, reaction mixture was cooled to room temperature and filtered through celite bed over Buchner funnel, celite bed was washed with DCM (2×300 mL). Combined filtrate was washed with water (300 mL) and aqueous sodium bicarbonate (120 mL), dried over sodium sulfate and concentrated under reduced pressure to afford off white solid (15.3 g, crude). Crude compound was purified by washing with n-pentane (2×150 mL) to get desired compound as white solid (9.5 g, impure). Impure title compound was used as such for the next reaction. 1H NMR (400 MHz, CDCl3) δ: 2.14 (t, J=5.8 Hz, 1H), 4.62 (d, J=5.8, 2H), 7.86 (d, J=1.32 Hz, 1H), 8.33 (d, J=3.32, 1H). LC-MS (m/z): 313.9 (M+H).

1. customResulting
2. customreaction mixture
3. temperaturewas refluxed for 10 hours
4. customAfter complete consumption of starting material, reaction mixture
5. filtrationfiltered through celite bed over Buchner funnel, celite bed
6. washwas washed with DCM (2×300 mL)
7. washCombined filtrate was washed with water (300 mL) and aqueous sodium bicarbonate (120 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customto afford off white solid (15.3 g, crude)
11. customCrude compound was purified
12. washby washing with n-pentane (2×150 mL)

ORD record

ord-a2f3ca8e179f484a94ab062dcb4907ab

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09131697B2