Toluene → HCID 66687355, compound

HRID 2201015Notes

Reaction equation

HRID 2201015 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[O:10][C:4]=2[CH:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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>[C:15]1([C:2]2[N:7]=[CH:6][C:5]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[O:10][C:4]=3[CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86663079HCID 86663079, compound

Product 1

HCID 66687355HCID 66687355, compoundYield 80.7%

Reagents, catalysts & solvents 2

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

Procedure

3-chlorobenzofuro[3,2-c]pyridine (2.89 g, 14 mmol), phenylboronic acid (2.56 g, 21 mmol), potassium phosphate (9.6 g, 42 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.45 g, 1.12 mmol) and Pd2(bda)3 (0.256 g, 0.28 mmol) were to toluene (100 mL) and water (10 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 washed with ethyl acetate 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 ethyl acetate and hexanes as the eluent. The solvent was removed to give 2.77 g of 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. washThe aqueous phase was washed with ethyl acetate
  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-08b8ce73d4c94021bdaa92ec1b1b3717
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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