Toluene → HCID 66757345, compound

HRID 1643179Notes

Reaction equation

HRID 1643179 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[S:11](N)(=[O:13])=[O:12].[C:15]([O-])([O-])=[O:16].[K+].[K+].[C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)#[N:22].[C:32]1(C)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CCO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][O:16][C:32]1[CH:37]=[CH:36][C:35]([S:11]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=3[C:26]3[CH:27]=[CH:28][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)[CH2:10][CH2:2]2)(=[O:13])=[O:12])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 66758161HCID 66758161, compound

Product 1

HCID 66757345HCID 66757345, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 11 (0.15 g, 0.40 mmol) in toluene (10 mL) was treated with tetrakis(triphenylphosphine) palladium (0.02 g, 0.02 mmol) under N2. An aqueous solution of K2CO3 (2 M, 1.4 mL) was then added, followed by a solution of 4-cyanophenylboronic acid (0.24 g, 1.63 mmol) in EtOH (8 mL). The resulting mixture was refluxed for 24 h. The solvent was removed and the residue was purified by flash chromatography (EtOAc:n-hexane=1:3) to afford Compound 17 (50.0 mg, 31%).

Workup

  1. temperatureThe resulting mixture was refluxed for 24 h
  2. customThe solvent was removed
  3. customthe residue was purified by flash chromatography (EtOAc:n-hexane=1:3)

Sources & evidence

ORD record
ord-2d6233629dd94dd0916da91ad6d495ec
Source dataset
uspto-grants-2012_02
Patent number
US08119683B2

Reaction notes

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