Cesium fluoride → HCID 68513860, compound

HRID 2091943Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[CH:17]([CH3:19])[CH3:18])(=O)=O.[CH3:22][NH:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].[F-].[Cs+]>O1CCOCC1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Pd]>[CH:17]([C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]([CH3:13])=[CH:12][C:7]=1[C:29]1[CH:30]=[CH:31][C:26]([C:24]([NH:23][CH3:22])=[O:25])=[CH:27][CH:28]=1)([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of crude 2-isopropyl-5-methyl-4-nitrophenyl trifluoromethanesulfonate (Step 2, 200 mg, 0.61 mmol), 4-(methylcarbamoyl)phenylboronic acid (142 mg, 0.79 mmol) and cesium fluoride (185 mg, 1.22 mmol) in dioxane (15 mL), is added palladium bis(tri-tert-butylphospine) (15 mg, 10% mmol) in a microwave tube. The tube is sealed. The mixture is purged with N2 for 3 min, and then heated at 120° C. for 10 min under microwave irradiation. The mixture is cooled, filtered and concentrated. The residue is purified with silica gel chromatography (60% ethyl acetate in hexanes) to afford white solid as 2′-isopropyl-N,5′-dimethyl-4′-nitrobiphenyl-4-carboxamide. ESMS m/z 313.2 (M+H+).

Workup

customThe tube is sealed
customThe mixture is purged with N2 for 3 min
temperatureThe mixture is cooled
filtrationfiltered
concentrationconcentrated
customThe residue is purified with silica gel chromatography (60% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d8314e79eaa8471f9febbd2159960b62
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440681B2

Reaction notes

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