Potassium Carbonate → 1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-3-nitro-1H-pyridin-2-one

HRID 2054587Notes

Reaction equation

[CH2:1]([N:8]1[CH:13]=[C:12](Br)[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[C:27]2[C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][C:23]=2[C:22]([C:32]2[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=2)=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH:13]=[C:12]([C:35]2[CH:36]=[CH:37][C:32]([C:22]3[C:23]4[O:24][C:25]5[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=5[C:27]=4[CH:19]=[CH:20][CH:21]=3)=[CH:33][CH:34]=2)[CH:11]=[C:10]([N+:15]([O-:17])=[O:16])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 1-benzyl-5-bromo-3-nitro-1H-pyridin-2-one (1.0 g, 3.24 mmol), 4-dibenzofuran-4-yl-phenyl-boronic acid (932 mg, 3.24 mmol), K2CO3 (1.34 g, 3 equiv., 9.7 mmol) in toluene (15 mL), ethanol (10 mL) and water (5 mL) was treated with treated with Pd(PPh3)4 (125 mg). After heating to 80° C. overnight, the solution was cooled to room temperature and the resulting solids were filtered and washed with ether (2×6 mL) to give 1-benzyl-5-(4-dibenzofuran-4-yl-phenyl)-3-nitro-1H-pyridin-2-one as a yellow solid (1.53 g, 92%).

Workup

temperaturethe solution was cooled to room temperature
filtrationthe resulting solids were filtered
washwashed with ether (2×6 mL)

Sources & evidence

ORD record: ord-058a88e42ad747cf89e27b4a7eacd22b
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329680B2

Reaction notes

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