Sodium Carbonate → HCID 68515276, compound

HRID 2091948Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([N+:14]([O-:16])=[O:15])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:17][NH:18][C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:13][O:12][C:10]1[CH:11]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([C:19](=[O:20])[NH:18][CH3:17])=[CH:22][CH:23]=2)[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

Conditions

Temperature: 40 °C

Procedure

Under nitrogen, the mixture of methyl 2-chloro-4-methoxy-5-nitrobenzoate (292 mg, 1.19 mmol), 4-(methylcarbamoyl)phenylboronic acid (319 mg, 1.79 mmol), dichlorobis(triphenylphosphine)palladium (II) (41 mg, 0.06 mmol) and sodium carbonate (378 mg, 3.57 mmol) in THF (8 mL) and water (2 mL) is heated at 40° C. overnight. The reaction mixture is cooled to room temperature and then partitioned between EtOAc and brine. The organic extracts are dried (Na2SO4), concentrated in vacuo, and purified by silica gel chromatography (EtOAc/Hexanes:1/3) to afford Methyl 5-methoxy-4′-(methylcarbamoyl)-4-nitrobiphenyl-2-carboxylate; ESMS m/z 345.1 (M+H+).

Workup

temperatureThe reaction mixture is cooled to room temperature
custompartitioned between EtOAc and brine
dry with materialThe organic extracts are dried (Na2SO4)
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (EtOAc/Hexanes:1/3)

Sources & evidence

ORD record: ord-d9a2fb3f938f47909ffe095859df8ffd
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440681B2

Reaction notes

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