2(3H)-Benzoxazolone → HCID 59627760, compound

HRID 418390Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9](I)[CH:10]=1)=[O:4].[O:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[NH:21][C:20]1=[O:28].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC>CN(C=O)C.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:8]=[C:9]([N:21]2[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:19][C:20]2=[O:28])[CH:10]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

5-Iodo-4′-methyl-biphenyl-3-carboxylic acid methyl ester (200 mg, 0.57 mmol) was dissolved in DMF (3 mL) and 2-benzoxazolinone (270 mg, 2.0 mmol), K3PO4 (424 mg, 2.0 mmol), CuI (15 mg), and 1,2-bis(methylamino)cyclohexane (0.15 mL) were added. The reaction mixture was stirred at 110° C. overnight, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified by preparative thin layer chromatography (3:1 hexanes/ethyl acetate) to give 4′-methyl-5-(2-oxo-benzooxazol-3-yl)-biphenyl-3-carboxylic acid methyl ester, which was used directly in the subsequent step.

Workup

temperaturecooled to room temperature
custompartitioned between water and ethyl acetate
concentrationThe organic layer was concentrated under reduced pressure
customthe residue was purified by preparative thin layer chromatography (3:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-75728a6496b5466faed0a38bcd4dbdcd
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093275B2

Reaction notes

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