Tetrahydrofuran → HCID 86600783, compound

Temperature

0 °C

To a solution of furan (13 g, 190 mmol) in anhydrous THF (150 mL) was added n-butyllithium (2.5 M in hexane, 40 mL, 100 mmol) at 0° C. under nitrogen. The solution was stirred at 0° C. for 30 minutes, cooled to −78° C., and treated with a solution of 1-(2-amino-5-bromophenyl)-2,2,3,3,3-pentafluoropropan-1-one. The mixture was allowed to warm to −30° C., a saturated ammonium chloride solution (100 mL) was added and mixture was warmed to rt. Ethyl acetate (300 mL) was added and organic layer separated, dried (MgSO4), and concentrated. The residue was dissolved in anhydrous THF. The resultant solution was cooled to 0° C., treated with triethylamine followed by addition of chloroacetyl chloride following the procedure described in example 1 to give N-{4-bromo-2-[2,2,3,3,3-pentafluoro-1-(2-furyl)-1-hydroxypropyl]phenyl}-2-chloroacetamide as a white solid. 1H NMR (DMSO-d6): δ 10.54 (s, 1H), 9.11 (s, 1H), 8.18 (d, J=9.0 Hz, 1H), 7.79 (m, 1H), 7.64 (dd, J=8.8, 2.4 Hz, 1H), 7.21 (d, J=1.7 Hz, 1H), 6.71 (s, 1H), 6.58 (m, 1H), 4.35 (d, J=1.5 Hz, 2H). MS (ESI) m/z 462/464 ([M+H]+); MS (ESI) m/z 460/462 ([M−H]−).

1. temperaturecooled to −78° C.
2. temperatureto warm to −30° C.
3. temperaturemixture was warmed to rt
4. customorganic layer separated
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. dissolutionThe residue was dissolved in anhydrous THF
8. temperatureThe resultant solution was cooled to 0° C.
9. additiontreated with triethylamine
10. additionfollowed by addition of chloroacetyl chloride following the procedure

ORD record

ord-2959a3dcf0f248188c23c12479949515

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598237B2