Diisopropylethylamine → HCID 70663467, compound

To a solution of 5-iodo-4-methyl-1H-pyrazole (0.5 g, 2.4 mmol, CAS RN 24086-18-8) in CH2Cl2 (5 mL) was added N,N-diisopropylethylamine (342 mg, 450 μL, 2.64 mmol) and benzyl chloromethyl ether (460 mg, 407 μL, 2.64 mmol, CAS RN 3587-60-8) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes and then poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL CH2Cl2. The layers were separated and the aqueous layer was extracted a second time with 30 mL CH2Cl2. The organic layers were washed with 30 mL brine, dried with MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 70:30). Colorless oil (610 mg, 77%). MS (ESI): m/z=329.014 [M+H]+.

1. customThe layers were separated
2. extractionthe aqueous layer was extracted a second time with 30 mL CH2Cl2
3. washThe organic layers were washed with 30 mL brine
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe compound was purified by silica gel chromatography
8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 70:30)

ORD record

ord-ada6b071bf234f72bcd6dbc47884415a

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987307B2