Ethanamine, 2,2,2-trifluoro- → 2-Iodo-N-(2,2,2-trifluoroethyl)furan-3-carboxamide

To a stirred solution of 2-iodofuran-3-carbonyl chloride (6.69 g, 26.1 mmol) in anhydrous tetrahydrofuran (120 ml) was added DIPEA (9.11 ml, 52.2 mmol) followed by 2,2,2-trifluoroethanamine (2.08 ml, 26.1 mmol) and the solution stirred for 1 h. The mixture was concentrated in vacuo. The residue was partitioned between 2M hydrochloric acid (aq) solution (100 ml) and dichloromethane (100 ml). The aqueous layer was separated and extracted with dichloromethane (2×100 ml). The combined organic layers were dried (phase separator) and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (gradient 0-50% ethyl acetate in cyclohexane) to afford the title compound (4.38 g, 53%). LCMS RT=0.98 min, M+H+=319.9.

1. concentrationThe mixture was concentrated in vacuo
2. customThe residue was partitioned between 2M hydrochloric acid (aq) solution (100 ml) and dichloromethane (100 ml)
3. customThe aqueous layer was separated
4. extractionextracted with dichloromethane (2×100 ml)
5. customThe combined organic layers were dried (phase separator)
6. concentrationconcentrated in vacuo
7. customThe resulting residue was purified by silica gel chromatography (gradient 0-50% ethyl acetate in cyclohexane)

ORD record

ord-5e9f3d8211584db497c477f9939d222f

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156853B2