Toluene → HCID 59500175, compound

HRID 1774092Notes

Reaction equation

HRID 1774092 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:8]1[C:16]2[C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[O:13][C:12]=2[C:11](B(O)O)=[CH:10][CH:9]=1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:20]1[C:14]2[O:13][C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:16]=3[C:15]=2[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 79732-BromopyridineHCID 2734328Dibenzofuran-4-boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 59500175HCID 59500175, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolvent

Procedure

To a 1 L round-bottom flask was added 2-bromopyridine (13.80 mL, 142 mmol), dibenzo[b,d]furan-4-ylboronic acid (25 g, 118 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.936 g, 4.72 mmol) and potassium phosphate tribasic monohydrate (81 g, 354 mmol) with toluene (350 mL) and water (35 mL). The reaction mixture was degassed with N2 for 20 minutes. Pd2(dba)3 (2.16 g, 2.35 mmol) was added and the reaction mixture was refluxed for 18 h. Completion of the reaction was confirmed by HPLC, GC and TLC. After cooling, the aqueous layer was removed and toluene was evaporated under reduced pressure. The residue was dissolved in dichloromethane and passed through one inch silica gel plug on a frit, eluting with dichloromethane. The crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane to give 18 g (62%) of the product. The product was confirmed by HPLC (99.6% purity) and GC/MS.

Workup

  1. customThe reaction mixture was degassed with N2 for 20 minutes
  2. temperaturethe reaction mixture was refluxed for 18 h
  3. temperatureAfter cooling
  4. customthe aqueous layer was removed
  5. customtoluene was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. washeluting with dichloromethane
  8. customThe crude product was chromatographed on silica gel with 20-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8837586a51844368b866bfbc08cbf9fe
Source dataset
uspto-grants-2016_02
Patent number
US09257658B2

Reaction notes

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