Ammonium Chloride → HCID 67246096, compound

Temperature

-60 °C

To a cold (−60° C.) solution of 2-methyl-6-(4-methyl-pyrazol-1-yl)-pyridine (0.52 g) (prepared by Reaction Condition 1 in Step i) in 14 mL of anhydrous THF was added 1.33 mL of a 2.5M solution of n-butyllithium (0.21 g) in hexanes. The reaction mixture was stirred at −60° C. for one hour. A 10 mL solution of N-bromosuccinimide (0.59 g) in THF was added and then the final solution was stirred at −60° C. for 2 hours. Saturated ammonium chloride (20 mL) was added and then the reaction mixture was allowed to warm to 24° C. The reaction mixture was diluted with 300 mL of ethyl acetate and then the aqueous phase was separated. The organic phase was washed with additional saturated ammonium chloride (50 mL) and then with brine (50 mL). The organic layer was separated, dried (sodium sulfate), filtered, and then the filtrate was evaporated to give a crude red oil. Purification by flash chromatography (silica gel, 20% ethyl acetate in heptane) provided, after drying, 0.377 g of the title compound as a yellow oil; 1H-NMR (400 MHz; DMSO-de) δ 7.88 (t, 1H), 7.69 (s, 1H), 7.44 (s, 1H), 7.32 (s, 1H), 2.50 (s, 3H), 2.02 (s, 3H); MS (APCI+) m/z 254 (MH+).

1. temperatureto warm to 24° C
2. customthe aqueous phase was separated
3. washThe organic phase was washed with additional saturated ammonium chloride (50 mL)
4. customThe organic layer was separated
5. dry with materialdried (sodium sulfate)
6. filtrationfiltered
7. customthe filtrate was evaporated
8. customto give a crude red oil
9. customPurification by flash chromatography (silica gel, 20% ethyl acetate in heptane)
10. customprovided
11. customafter drying

ORD record

ord-5e8ba2040f4647e5bcb2febc9c9435a4

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090625B2