Potassium Carbonate → 3-(4-(Benzyloxy)phenyl)pyridine

HRID 1909711Notes

Reaction equation

HRID 1909711 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CCO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 707143-IodopyridineHCID 27343144-Benzyloxy-phenylboronic acid

Product 1

HCID 672269493-(4-(Benzyloxy)phenyl)pyridineYield 92%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent3×

Conditions

Temperature
90 °C

Procedure

To a solution of 4-benzyloxyphenylboronic acid (1.48 g, 6.5 mmol) in DME (10 mL) was added 3-iodo pyridine (1.03 g, 5.0 mmol) in DME (8 mL), potassium carbonate (2.0 g, 15 mmol) in 1:1 mixture of EtOH:water (3 mL), palladium(II) acetate (56 mg, 0.25 mmol), and triphenyl phosphine (202 mg, 1.0 mmol) in DME (2 mL). The resulting mixture was warmed up to 90° C. and stirred for 16 h at that temperature. After cooling to rt, reaction mixture was poured into ice-water (200 mL) and product was extracted with EtOAc, washed with brine, filtered through pad of Celite and concentrated to a yellow solid. The crude mixture was purified by silica gel flash chromatography (20% EtOAc/Hexane) to obtain the title product as yellow solid (1.2 g, 92%).

Workup

  1. temperatureAfter cooling to rt
  2. customreaction mixture
  3. extractionwas extracted with EtOAc
  4. washwashed with brine
  5. filtrationfiltered through pad of Celite
  6. concentrationconcentrated to a yellow solid
  7. customThe crude mixture was purified by silica gel flash chromatography (20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-eb42ef77d61f4bc585f587b84e6d1c00
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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