Toluene → HCID 67520692, compound

HRID 1925685Notes

Reaction equation

HRID 1925685 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[S:12]([N:15]([C:19]1[CH:23]=[CH:22][S:21][C:20]=1[C:24]([O:26][CH3:27])=[O:25])[CH2:16][O:17][CH3:18])(=[O:14])=[O:13].[C:28]1(/[CH:34]=[CH:35]/B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>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.C(O)C>[C:8]([C:6]1[CH:5]=[CH:4][C:3]([S:12]([N:15]([C:19]2[CH:23]=[CH:22][S:21][C:20]=2[C:24]([O:26][CH3:27])=[O:25])[CH2:16][O:17][CH3:18])(=[O:14])=[O:13])=[C:2]([CH:35]=[CH:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 5702628Styrylboronic acidHCID 59180400HCID 59180400, compound

Product 1

HCID 67520692HCID 67520692, compoundYield 62.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 2.5-5.0 mL microwave reaction tube was successively charged with 6 (200.0 mg, 0.43 mmol), trans-2-phenylvinylboronic acid (96.0 mg; 0.65 mmol), cesium carbonate (420.0 mg; 1.30 mmol), tetrakis(triphenylphosphine)palladium(0) (25.0 mg; 0.022 mmol), toluene (1.3 mL), ethanol (1.3 mL) and water (1.3 mL). The reaction tube was purged with nitrogen and subjected to the following microwave conditions: Temperature=140° C.; Power=250 W; Time=15 minutes; Cooling On; Absorption Very High. The reaction mixture was allowed to cool to room temperature and then was diluted with ethyl acetate (15 mL) and washed with aqueous hydrochloric acid (3×10 mL; 2N). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude dark oil residue was purified by automated silica gel column chromatography (Biotage®) eluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution) to give the title product as a white solid (134 mg).

Workup

  1. customThe reaction tube was purged with nitrogen
  2. customTemperature=140° C.
  3. customTime=15 minutes
  4. temperatureCooling On
  5. customAbsorption Very High
  6. additionwas diluted with ethyl acetate (15 mL)
  7. washwashed with aqueous hydrochloric acid (3×10 mL; 2N)
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude dark oil residue was purified by automated silica gel column chromatography (Biotage®)
  12. washeluting with ethyl acetate/hexanes (0 to 30% v/v over 400 mL gradient elution)

Sources & evidence

ORD record
ord-2994b53dfa8d40c98e7d8c02cd75085c
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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