Sodium Carbonate → Ethyl 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylate

HRID 714958Notes

Reaction equation

I[C:2]1[O:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O.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]>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:4]2[O:3][C:2]([C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)=[N:6][C:5]=2[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of ethyl 2-iodo-5-(4-methoxyphenyl)oxazole-4-carboxylate (0.100 g, 0.27 mmol) and 2-thiophenyl boronic acid (0.069 g, 0.54 mmol) in acetonitrile (2 mL) was added a solution of Pd(dppf)2Cl2 (0.010 g, 0.012 mmol) in acetonitrile (0.2 mL) followed by 1M aqueous sodium carbonate solution (0.535 mL, 0.54 mmol). The resulting reaction mixture was heated at 150° C. in the microwave for 15 minutes and the solvent was then removed in vacuo. The residue was purified by silica gel column chromatography using a gradient of 4-90% EtOAc in hexanes to afford ethyl 5-(4-methoxyphenyl)-2-(thiophen-2-yl)oxazole-4-carboxylate which was used without further purification. LCMS (1) Rt: 2.45 min; m/z (ES+) 330.

Workup

customThe resulting reaction mixture
customthe solvent was then removed in vacuo
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-2ed28671ebdb4dfcb3365244575ea131
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187465B2

Reaction notes

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