2-Bromoethanol → HCID 57886737, compound

A solution of 4-iodo-1H-pyrazole (4.50 g, 23.20 mmol) in DMF (45 mL) was treated with sodium hydride (60% w/w, 1.42 g, 35.5 mmol) at 0° C. and stirred at room temperature. After 1 hour the resulting mixture was treated with 2-bromoethanol (2.5 mL, 35.2 mmol) at 0° C. The resulting mixture was heated to 65° C. for 3 days. The reaction quenched with brine/EtOAc and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water, brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 50% EtOAc in cyclohexane to give the title compound (3.55 g, 64%).

1. temperatureThe resulting mixture was heated to 65° C. for 3 days
2. customThe reaction quenched with brine/EtOAc
3. extractionthe aqueous layer extracted with EtOAc
4. washThe combined organic layers were washed with water, brine
5. customdried
6. concentrationconcentrated
7. customThe residue was purified by silica gel column chromatography
8. washeluting with 0 to 50% EtOAc in cyclohexane

ORD record

ord-2a68d8895f8d4351ab3702943d18515e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409907B2