Chlorosuccinimide → HCID 178507360, compound

A mixture of 5-aminoindazole (1.373 g, 10.00 mmol) and N-chlorosuccinimide (1.381 g, 10.14 mmol) in methylene chloride (50 mL) was sonicated at rt for 30 min. The brown mixture was then stirred overnight at rt. The suspension was diluted with CH2Cl2 to ≈100 mL, water and aq. K2CO3 solution were added, and the insoluble brown material was filtered off and washed with CH2Cl2 and water. The layers of the filtrate were separated; the organic layer was washed with water (3×) and brine and dried over MgSO4. The dried solution was filtered through a pad of silica gel, washing with 5% MeOH in CH2Cl2 until no more product eluted as indicated by TLC. Concentrating and drying in vacuo gave the title compound as yellow solid. MS (ES+): m/z 168.2/170.2 (100/37) [MH+]. HPLC: tR=2.1 min (ZQ2000, polar—5 min). 1H NMR (CDCl3, 400 MHz): δ=5.06 (s, 2H), 6.96 (d, J=8.5 Hz, 1H), 7.27 (d, J=8.5 Hz, 1H), 7.78 (s, 1H), 12.95 (brs, 1H).

1. customwas sonicated at rt for 30 min
2. additionwere added
3. filtrationthe insoluble brown material was filtered off
4. washwashed with CH2Cl2 and water
5. customThe layers of the filtrate were separated
6. washthe organic layer was washed with water (3×) and brine
7. dry with materialdried over MgSO4
8. filtrationThe dried solution was filtered through a pad of silica gel
9. washwashing with 5% MeOH in CH2Cl2 until no more product
10. washeluted
11. concentrationConcentrating
12. customdrying in vacuo

ORD record

ord-0105245aab324ae4af4bb0deff203a74

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465726B2