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

HRID 2406892Notes

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-fd1e310359054e6b85c851e211997b80
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809402B2

Reaction notes

Loading…