1,2-Dimethoxyethane → HCID 71236373, compound

HRID 2369730Notes

Reaction equation

HRID 2369730 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]=[CH:22][C:21]([Cl:24])=[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:21]1[CH:22]=[CH:23][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)=[N:19][CH:20]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 276852,5-DichloropyridineHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 71236373HCID 71236373, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Dibenzo[b,d]furan-4-ylboronic acid (9.5 g, 44.8 mmol), 2,5-dichloropyridine (7.0 g, 47.0 mmol), Pd(PPh3)4 (2.6 g, 2.2 mmol) and potassium carbonate (18.6 g, 134 mmol) were added to dimethoxyethane (75 mL) and water (75 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 11.7 g of crude product. The product was crystallized from hexane to give 9.5 g (76%) of 5-chloro-2-(dibenzo[b,d]furan-4-yl)pyridine as white needles. The product was confirmed by GC/MS.

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 11.7 g of crude product
  11. customThe product was crystallized from hexane

Sources & evidence

ORD record
ord-5a6e59021f62482588d57eca910e9c2d
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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