1,2-Dimethoxyethane → HCID 71007915, compound

HRID 2369733Notes

Reaction equation

HRID 2369733 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[CH:10]1[C:18]2[C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[C:13](B(O)O)=[CH:12][CH:11]=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>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:22]2[C:16]3[O:15][C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:18]=4[C:17]=3[CH:19]=[CH:20][CH:21]=2)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734328Dibenzofuran-4-boronic acidHCID 27344292,5-Dibromo-4-methylpyridine

Product 1

HCID 71007915HCID 71007915, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

2,5-Dibromo-4-methylpyridine (30 g, 118 mmol), dibenzo[b,d]furan-4-ylboronic acid (25 g, 118 mmol), Pd(PPh3)4 (1.4 g, 1.18 mmol), and K2CO3 (49 g, 354 mmol) were added to a flask with dimethoxyethane (450 mL) and water (100 mL) and degassed with nitrogen. The reaction mixture was heated to reflux for 15 h before cooling to room temperature. 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 and 29.7 g of crude product was obtained. The product was crystallized from hexane to give 28.8 g (72%) of pure product. The product was confirmed by NMR and HPLC (99.3% pure)

Workup

  1. customdegassed with nitrogen
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 15 h
  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. custom29.7 g of crude product was obtained
  11. customThe product was crystallized from hexane

Sources & evidence

ORD record
ord-d1aac974cdce4a36afc85d0ef1e1d73f
Source dataset
uspto-grants-2014_04
Patent number
US08709615B2

Reaction notes

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