1,2-Dichloroethane → 5-(4-(2-Chloroethoxy)phenyl)-2-(2,6-difluorophenyl)oxazole-4-carboxamide

HRID 715001Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[C:12]([C:14]([NH2:16])=[O:15])[N:13]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:30][CH2:31][CH2:32]Cl>CN(C=O)C.CCOC(C)=O>[Cl:30][CH2:31][CH2:32][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:11]2[O:10][C:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:13][C:12]=2[C:14]([NH2:16])=[O:15])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(2,6-difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamide (0.100 g, 0.316 mmol) in DMF (5 ml) were added potassium carbonate (0.220 g, 1.58 mmol) and 1,2-dichloroethane (0.50 ml, 6.32 mmol). The reaction was heated to 130° C. via microwave irradiation and held at that temperature for 1 hour. The reaction was then diluted with EtOAc, washed with water and brine and dried over Na2SO4 before being concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using 0-50% EtOAc in hexane as eluant to afford 5-(4-(2-chloroethoxy)phenyl)-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.11 g, 0.29 mmol, 92%) as a white solid. LCMS (1) 2.25 min; m/z (ES+) 379/381.

Workup

washwashed with water and brine
dry with materialdried over Na2SO4
concentrationbefore being concentrated in vacuo
customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-e254a5be76fb45e5b61bb3dd226681b4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187465B2

Reaction notes

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