Toluene → HCID 66687323, compound

HRID 2201020Notes

Reaction equation

HRID 2201020 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[C:11]1([C:17]2[N:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:20]1[CH:19]=[CH:18][C:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:22][CH:21]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 69115o-IodonitrobenzeneHCID 2762710(6-Phenylpyridin-3-yl)boronic acid

Product 1

HCID 66687323HCID 66687323, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolvent

Procedure

2-Iodo-1-nitrobenzene (6.88 g, 27.64 mmol), 6-phenyl-3-pyridinylboronic acid (5.5 g, 27.64 mmol), potassium phosphate (17.6 g, 82.91 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.451 g, 0.522 mmol) and Pd2(bda)3 (0.119 g, 0.55 mmol) were to toluene (150 mL) and water (12 mL). Nitrogen was bubbled through the solution for 30 minutes and then the solution was refluxed for overnight in an atmosphere of nitrogen. The reaction was then allowed to cool to room temperature and the organic phase was separated from the aqueous phase. The aqueous phase was extracted with ethylacetate and the organic fractions were combined and dried over sodium sulfate and the solvent removed under vacuum. The product was chromatographed using silica gel with ethylacetate and hexanes as the eluent. The solvent was removed to give 5.02 g of the title compound.

Workup

  1. customNitrogen was bubbled through the solution for 30 minutes
  2. temperaturethe solution was refluxed for overnight in an atmosphere of nitrogen
  3. customthe organic phase was separated from the aqueous phase
  4. extractionThe aqueous phase was extracted with ethylacetate
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed under vacuum
  7. customThe product was chromatographed
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-9378ef9515b548f4afc4380f4a687405
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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