Potassium Carbonate → 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(2-oxooxazolidin-3-yl)benzofuran-3-carboxamide

HRID 1776919Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:22][C:23](=[O:28])[O:24][CH2:25][CH2:26]Cl)=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17](=[O:20])[NH:18][CH3:19])[C:6]=2[CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([N:22]2[CH2:26][CH2:25][O:24][C:23]2=[O:28])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([NH:18][CH3:19])=[O:20])[C:6]=2[CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-chloroethyl (5-bromo-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)carbamate (1.00 g, 2.10 mmol) was added to a mixture of KI (0.40 g, 2.10 mmol) and K2CO3 (0.75 g, 6.30 mmol) in DMF (20 mL) and the mixture was stirred under N2 protection at 110° C. for 2 hours. After concentrated in vacuo, the resulting residue was washed with water and EtOAc to provide 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(2-oxooxazolidin-3-yl)benzofuran-3-carboxamide (408 mg, yield: 45%). 1H-NMR (CDCl3, 400 MHz) δ 7.58 (s, 1H), 7.51 (m, 2H), 7.19 (s, 1H), 7.11˜7.13 (d, J=8.0 Hz, 1H), 6.83˜6.88 (m, 1H), 4.37˜7.41 (m, 2H), 4.12˜4.14 (m, 2H), 3.00 (d, J=4.8 Hz, 3H). MS (M+H)+: 433/435.

Workup

concentrationAfter concentrated in vacuo
washthe resulting residue was washed with water and EtOAc

Sources & evidence

ORD record: ord-4ea7424c1de9459a8e4200e6a2e85edc
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

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