Water → Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate

HRID 1892564Notes

Reaction equation

HRID 1892564 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([N+:27]([O-:29])=[O:28])=[CH:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[C:12]([C:22](=[O:25])[NH:23][CH3:24])[C:11]=2[CH:26]=1)(=O)=O.[CH3:32][O:33][C:34]1[CH:43]=[CH:42][C:41](B2OC(C)(C)C(C)(C)O2)=[CH:40][C:35]=1[C:36]([O:38][CH3:39])=[O:37].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:14][C:10]3[CH:9]=[C:8]([N+:27]([O-:29])=[O:28])[C:7]([C:41]4[CH:42]=[CH:43][C:34]([O:33][CH3:32])=[C:35]([CH:40]=4)[C:36]([O:38][CH3:39])=[O:37])=[CH:26][C:11]=3[C:12]=2[C:22](=[O:25])[NH:23][CH3:24])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 22930502Methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 592753912-(4-Fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl trifluoromethanesulfonate

Product 1

HCID 67957912Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl trifluoromethanesulfonate (750 mg, 1.622 mmol), methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (569 mg, 1.947 mmol) and cesium carbonate (1057 mg, 3.24 mmol) in dioxane (20 mL)/water (1.0 mL) at rt under nitrogen was added Pd(PPh3)4(0) (187 mg, 0.162 mmol). The reaction mixture was heated to 100° C. and maintained at the same temperature for overnight. The reaction mixture was filtered through celite, and the celite bed washed with ethyl acetate. The filtrate was concentrated and the residue purified by Combiflash using MeOH/CHCl3 as eluant. The desired fraction was collected at 2.5% MeOH in CHCl3. Yield: 0.650 g (83%).

Workup

  1. temperaturemaintained at the same temperature for overnight
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe celite bed washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue purified by Combiflash
  6. customThe desired fraction was collected at 2.5% MeOH in CHCl3

Sources & evidence

ORD record
ord-878e697e8a1e44fa81a9e6815f6c4c73
Source dataset
uspto-grants-2013_08
Patent number
US08507683B2

Reaction notes

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