Cesium carbonate → HCID 67107511, compound

HRID 2177731Notes

Reaction equation

HRID 2177731 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14](B3OC(C)(C)C(C)(C)O3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:39]1[CH:40]=[N:41][S:42][CH:43]=1>O1CCOCC1.O.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]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([C:39]3[CH:40]=[N:41][S:42][CH:43]=3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 52003584-Bromo-isothiazoleHCID 67107706HCID 67107706, compound2×

Product 1

HCID 67107511HCID 67107511, compoundYield 32.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Intermediate 59, 0.15 g), tri-tert-butyl-phosphinium tetrafluoroborate (0.01 g), cesium carbonate (0.34 g), tris-(dibenzylideneacetone)-dipalladium (0.016 g), and 4-bromoisothiazole (0.06 g) in dioxane (3.2 ml) and water (0.4 ml) was degassed and then heated in the microwave at 120° C. for 20 minutes. After cooling, the mixture was diluted with ether, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60% to give crude methyl 6-(benzenesulphonylmethyl)-3-(isothiazol-4-yl)-2-methoxy-benzoate (0.044 g) as an oil. The material was used without further purification or characterisation.

Workup

  1. customwas degassed
  2. temperatureAfter cooling
  3. additionthe mixture was diluted with ether
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-60%

Sources & evidence

ORD record
ord-381db1f52bfe47259a321107be560c20
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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