1,2-Dimethoxyethane → HCID 71236365, compound

HRID 2369732Notes

Reaction equation

HRID 2369732 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Cl[C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].C(COC)OC>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>[Cl:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 335152,4-DichloropyridineHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 71236365HCID 71236365, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Dibenzo[b,d]furan-4-ylboronic acid (25 g, 118 mmol), 2,4-dichloropyridine (19.2 g, 130 mmol), Pd(PPh3)4 (4.1 g, 3.5 mmol) and potassium carbonate (48.9 g, 354 mmol) were added to dimethoxyethane (200 mL) and water (200 mL). The reaction mixture was degassed with nitrogen before being heated to reflux overnight. EtOAc and water were added, the organic layer separated and the aqueous layer was extracted with 3×50 mL dichloromethane and dried over sodium sulfate. After removing the solvent under reduced pressure, the crude product was chromatographed on silica gel with dichloromethane to yield 33.4 g of crude product. The product was crystallized from hexane to give 27.0 g (82%) of 4-chloro-2-(dibenzo[b,d]furan-4-yl)pyridine as white needles. The product was confirmed by GC/MS and NMR.

Workup

  1. customThe reaction mixture was degassed with nitrogen
  2. temperaturebefore being heated
  3. temperatureto reflux overnight
  4. additionEtOAc and water were added
  5. customthe organic layer separated
  6. extractionthe aqueous layer was extracted with 3×50 mL dichloromethane
  7. dry with materialdried over sodium sulfate
  8. customAfter removing the solvent under reduced pressure
  9. customthe crude product was chromatographed on silica gel with dichloromethane
  10. customto yield 33.4 g of crude product
  11. customThe product was crystallized from hexane

Sources & evidence

ORD record
ord-4c37b04c6abf4a0fad48c47422a9128a
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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