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Sodium Carbonate → 2-(2,6-Difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamide

HRID 715000
Notes
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Reaction equation

HRID 715000 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH2:17])=[O:16].[OH:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.CCOC(C)=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([F:13])[C:7]=1[C:5]1[O:6][C:2]([C:22]2[CH:23]=[CH:24][C:19]([OH:18])=[CH:20][CH:21]=2)=[C:3]([C:15]([NH2:17])=[O:16])[N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 595875995-Bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamide

Product 1

HCID 595875782-(2,6-Difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamideYield 80%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 6342AcetonitrileSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 5-bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.060 g, 0.20 mmol), 4-hydroxyphenylboronic acid (0.055 g, 0.40 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (0.008 g, 0.01 mmol) in MeCN (4 ml) was added 1M aqueous Na2CO3 (0.4 ml, 0.4 mmol). The reaction was heated via microwave irradiation to 150° C. and held at this temperature for 15 minutes. The reaction was then diluted with EtOAc and washed with 2M HCl. The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using 5-70% EtOAc in hexane as eluant to furnish 2-(2,6-difluorophenyl)-5-(4-hydroxyphenyl)oxazole-4-carboxamide (0.050 g, 0.16 mmol, 80%) as an off white powder. LCMS (1) 1.73 min; m/z (ES−) 315.

Workup

  1. washwashed with 2M HCl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-f1b23cb8175e4db2aad8640fd58950b3
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187465B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes