Toluene → HCID 58188319, compound

HRID 1845239Notes

Reaction equation

HRID 1845239 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.O>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:12]=[C:11]([C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 79599(4-Bromophenyl)boronic acidHCID 58188281HCID 58188281, compound

Product 1

HCID 58188319HCID 58188319, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

To a mixture of ethyl 3-bromo-5-(pyrrolidine-1-carbonyl)benzoate (3.20 g, 9.81 mmol), 4-bromophenylboronic acid (2.17 g, 10.8 mmol), toluene (40 mL), cesium carbonate (3.52 g, 10.8 mmol), and water (5 mL) under argon was added tetrakis(triphenylphosphine)palladium(0) (567 mg, 0.49 mmol). The mixture was heated under reflux for 15 h. After cooling, the mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (0-80% EtOAc/hexane) to afford a syrup. LC-MS: 404.0 [M+1]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. washthe filter cake was washed with EtOAc
  6. washThe filtrate was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column (0-80% EtOAc/hexane)
  10. customto afford a syrup

Sources & evidence

ORD record
ord-5abec3ab816b41e4a5c8ecb854e30f26
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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