Cesium carbonate → 6-(Benzenesulphonylmethyl)-3-(furan-2-yl)-2-methoxybenzoic acid

HRID 2177674Notes

Reaction equation

HRID 2177674 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.COC(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:20][CH3:21])[C:14]([C:24]3[O:23][CH:27]=[CH:26][CH:25]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 2734357Furan-2-boronic acidHCID 529139736-(Benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid

Product 1

HCID 529142926-(Benzenesulphonylmethyl)-3-(furan-2-yl)-2-methoxybenzoic acidYield 33.1%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Example 7, 0.1 g), 2-furylboronic acid (0.031 g), tri-tert-butylphosphinium tetrafluoroborate (0.0074 g), cesium carbonate (0.253 g) and tris-(dibenzylideneacetone)dipalladium (0.012 g) in dioxane (3 ml) and water (0.4 ml) was sealed in a vial under nitrogen and heated at 80° C. for 2 hours. After cooling, the mixture was diluted with t-butyl methyl ether, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified twice by preparative HPLC (C18), eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 25-98% to give 6-(benzenesulphonylmethyl)-3-(furan-2-yl)-2-methoxybenzoic acid (0.032 g) as a white solid.

Workup

  1. customwas sealed in a vial under nitrogen
  2. temperatureAfter cooling
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified twice by preparative HPLC (C18)
  7. washeluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 25-98%

Sources & evidence

ORD record
ord-13b0fc92ce6240308a38519eadcdebd0
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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