1,2-Dimethoxyethane → HCID 15509101, compound

HRID 324937Notes

Reaction equation

HRID 324937 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[CH3:10][O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]([O:22][CH3:23])[C:13]=1Br.C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:13]2[C:14]([O:22][CH3:23])=[CH:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]=2[O:11][CH3:10])[CH:2]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 15509100HCID 15509100, compound

Product 1

HCID 15509101HCID 15509101, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine-3-boronic acid (3.94 g 32 mmol, Frontier Scientific, Inc.), 1,3-dimethoxy -2-bromonaphthalene 8 (6.6 g, 24.7 mmol), glyme (200 ml), and tetrakis(triphenylphosphine) palladium (Ph3P)4Pd (3 g, 2.7 mmol) were stirred for 15 minutes followed by the addition of potassium carbonate (11.4 g in 50 mL of water). After refluxing over-night, the reaction mixture was poured into 800 ml of 1:1 water:ethyl acetate. The organic layer was washed with water (300 ml×2) and brine (200 ml), solvent was removed, and the crude product was purified by silica-gel chromatography eluting with dichloromethane and acetone (0% to 5% acetone) yielding 5.1 g (84%) of 9.

Workup

  1. temperatureAfter refluxing over-night
  2. washThe organic layer was washed with water (300 ml×2) and brine (200 ml), solvent
  3. customwas removed
  4. customthe crude product was purified by silica-gel chromatography
  5. washeluting with dichloromethane and acetone (0% to 5% acetone)

Sources & evidence

ORD record
ord-3ab37a5f28e449d4ad8275f1ca569ee6
Source dataset
uspto-grants-2001_04
Patent number
US06221604B1

Reaction notes

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