Isovaleryl chloride → HCID 68509241, compound

A mixture of 5-bromo-2-hydrazinopyridine (1.00 g, 5.00 mmol; Frontier) and isovaleryl chloride (5.50 mL, 45.1 mmol) was heated at reflux for about 3 h. The reaction was cooled to ambient temperature then heptane (5 mL) was added and the reaction was stirred for about 15 min. The mixture was filtered, washing with additional heptane, and suspended in water/DCM (1:1, 20 mL) then added 1N NaOH (3.5 mL). This mixture was stirred for about 15 min. The layers were separated and the aqueous layer was extracted with DCM (2×10 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound (0.86 g, 65%): LC/MS (Table 1, Method b) Rt, =1.87 min; MS m/z: 254.0 (M+H)+.

1. temperaturewas heated
2. temperatureat reflux for about 3 h
3. filtrationThe mixture was filtered
4. washwashing with additional heptane
5. additionthen added 1N NaOH (3.5 mL)
6. stirringThis mixture was stirred for about 15 min
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with DCM (2×10 mL)
9. washThe combined organic layers were washed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-cec7b43f68c447fd94eea1d3cd551cd4

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790741B2