Hexachloroethane → HCID 86717496, compound

Temperature

-78 °C

Into a 1-neck round-bottom flask N,N-diisopropylamine (0.50 mL, 3.6 mmol) was dissolved in tetrahydrofuran (4.0 mL) and cooled at −78° C. 1.6 M n-butyllithium in hexane (1.9 mL, 3.1 mmol) was added. The reaction was stirred at −78° C. for 30 min and 6-bromo-2-methylimidazo[1,2-a]pyrazine (from Ark Pharm, 0.500 g, 2.36 mmol) in tetrahydrofuran (6.0 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 45 min and hexachloroethane (0.72 g, 3.1 mmol) was added. The resulting mixture was stirred at −78° C. for 1 h. The reaction was quenched with NH4Cl solution and then partitioned between EtOAc and water. The EtOAc extract was washed with brine, dried (MgSO4), and stripped in vacuo. The residue was chromatographed on silica gel eluting with 40% EtOAc in hexanes to give the desired product (0.25 g, 43%). LCMS calculated for C7H6BrClN3 (M+H)+: m/z=245.9. Found: 245.9. 1H NMR (CDCl3, 400 MHz) δ 8.72 (1H, s), 7.68 (1H, s), 2.56 (3H, s) ppm.

1. stirringThe reaction mixture was stirred at −78° C. for 45 min
2. stirringThe resulting mixture was stirred at −78° C. for 1 h
3. customThe reaction was quenched with NH4Cl solution
4. custompartitioned between EtOAc and water
5. extractionThe EtOAc extract
6. washwas washed with brine
7. dry with materialdried (MgSO4)
8. customThe residue was chromatographed on silica gel eluting with 40% EtOAc in hexanes

ORD record

ord-698b17ab0f344ad7b6e6bc20a4a3524e

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181271B2