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

HRID 389769
Notes
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Reaction equation

HRID 389769 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 11430Potassium CarbonateHCID 595875782-(2,6-Difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamide

Product 1

HCID 595873755-(4-(2-Chloroethoxy)phenyl)-2-(2,6-difluorophenyl)oxazole-4-carboxamideYield 92%

Reagents, catalysts & solvents 2

HCID 6228Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

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

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

Sources & evidence

ORD record
ord-d941bc281b2d46c8b955c0e14a8bf96e
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08378095B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes