Toluene → HCID 58188011, compound

HRID 1845245Notes

Reaction equation

HRID 1845245 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=[O:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].B(O)(O)[C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:15]1([S:12]([C:10]2[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=[C:2]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[CH:11]=2)(=[O:14])=[O:13])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 58188059HCID 58188059, compound

Product 1

HCID 58188011HCID 58188011, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A microwave vial was charged with methyl 3-bromo-5-(cyclopentylsulfonyl)benzoate (0.50 g, 1.44 mmol), p-tolylboronic acid (0.44 g, 3.25 mmol), toluene (7 mL), and a solution of cesium carbonate (1.06 g, 3.26 mmol) in water (0.3 mL). The vial was degassed and purged with argon, and then tetrakis(triphenylphosphine)palladium(0) (0.16 g, 0.14 mmol) was added. The reaction mixture was subjected to microwave irradiation at 100° C. for 2 h. After cooling, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified via flash column (0-25% EtOAc/hexane) to yield the title compound as a colorless oil.

Workup

  1. customThe vial was degassed
  2. custompurged with argon
  3. customirradiation at 100° C. for 2 h
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified via flash column (0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-742ef734c5064a61b892334faba8e29f
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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