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

HRID 1410443
Notes
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Reaction equation

HRID 1410443 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].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[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:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:3]([C:15]([NH2:17])=[O:16])[N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 595875995-Bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamide

Product 1

HCID 251196542-(2,6-Difluorophenyl)-5-phenyloxazole-4-carboxamideYield 10%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

A mixture of 5-bromo-2-(2,6-difluorophenyl)oxazole-4-carboxamide (0.060 g, 0.2 mmol), phenyl boronic acid (0.048 g, 0.4 mmol), Pd(dppf)2Cl2 (0.008 g, 0.01 mmol) and 1M sodium carbonate solution (0.395 mL, 0.4 mmol) in acetonitrile (4 mL) was heated in the microwave at 150° C. for 15 minutes. The reaction mixture was partitioned between 1M sodium hydroxide solution and EtOAc and the aqueous phase washed with EtOAc. The organic phase was passed through a MP-SH resin cartridge. (0.5 g) and the solvent removed in vacuo. The residue was purified by preparative HPLC to afford 2-(2,6-difluorophenyl)-5-phenyloxazole-4-carboxamide (0.0047 g, 0.02 mmol, 8%) as a white solid. 1H NMR (DMSO) δ 7.40 (2H, t,), 7.54 (3H, m), 7.75 (3H, m), 8.24 (2H, m). LCMS (2) Rt: 2.89 min; m/z (ES+) 301.

Workup

  1. customThe reaction mixture was partitioned between 1M sodium hydroxide solution and EtOAc
  2. washthe aqueous phase washed with EtOAc
  3. custom(0.5 g) and the solvent removed in vacuo
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-7752955debb84de6aa7f594be4d687fd
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921544B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes