Phenol → HCID 69883467, compound

HRID 2120352Notes

Reaction equation

[Cl:1][C:2]1[C:7](F)=[C:6]([S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:23])[C@:16]([OH:22])([CH3:21])[C:17]([F:20])([F:19])[F:18].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:6]([S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:23])[C@:16]([OH:22])([CH3:21])[C:17]([F:20])([F:19])[F:18]

Participants

Conditions

Temperature: 150 °C

Procedure

(R)-N-[2-Chloro-3-fluoro-4-(ethylsulphonyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 15; 0.308 g) was added to a stirred suspension of phenol (0.150 g) and anhydrous potassium carbonate (0.220 g) in anhydrous DMF (2 ml). The reaction mixture was heated to 150° C. under argon for 17 hours and allowed to cool to ambient temperature. EtOAc (50 ml) was added and the organic phase was washed with brine (4×50 ml), separated, dried and volatile material was removed by evaporation. The residue was purified on a 8 g silica Biotage cartridge eluting 40% EtOAc/isohexane to give the title compound (0.073 g) as a pale yellow foam. NMR (CDCl3): 1.18 (t, 3H), 1.69 (s, 3H), 3.23-3.30 (q, 2H), 3.48 (s, 1H), 6.78 (d, 2H), 7.02 (t, 1H), 7.24 (t, 2H), 7.97 (d, 1), 8.50 (d, 1H), 9.24 (brs, 1H); m/z: 450.

Workup

temperatureto cool to ambient temperature
washthe organic phase was washed with brine (4×50 ml)
customseparated
customdried
customvolatile material was removed by evaporation
customThe residue was purified on a 8 g silica Biotage cartridge
washeluting 40% EtOAc/isohexane

Sources & evidence

ORD record: ord-1da91b876204447db06a3d07f77dc5c7
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689909B1

Reaction notes

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