Sodium Bicarbonate → 3-[(Benzoxazol-2-yl)methoxy]-5-ethyl-6-methylpyridin-2(1H)-one

HRID 1033009Notes

Reaction equation

HRID 1033009 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:13]([O:21]C)=[N:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1.[B].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:13](=[O:21])[NH:14][C:15]([CH3:20])=[C:16]([CH2:18][CH3:19])[CH:17]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5462311BoronHCID 103348493-[(Benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine

Product 1

HCID 4548203-[(Benzoxazol-2-yl)methoxy]-5-ethyl-6-methylpyridin-2(1H)-oneYield 51.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

3[(Benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine (140 mg, 0.47 mmol) was dissolved in methylene chloride (5 ml) and cooled in an ice bath under an atmosphere of nitrogen. 1M Boron tribomide (2.3 mL, 2.3 mmol) in hexane was added to this solution and the reaction mixture was allowed to warm to room temperature over a 0.75 hour period. This mixture was re-cooled in an ice bath and saturated aqueous NaHCO3 (5 mL) was added to quench the reaction. The methylene chloride layer was dried (Na2SO4), filtered and evaporated. The residue was triturated with diethyl ether to give 69 mg of crude product. Recrystallization from methanol yielded 60 mg (45%), m.p. 198°-200° C.

Workup

  1. temperaturecooled in an ice bath under an atmosphere of nitrogen
  2. temperatureThis mixture was re-cooled in an ice bath
  3. customto quench
  4. customthe reaction
  5. dry with materialThe methylene chloride layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3e0a6ec88a12424795066a833e2c57c6
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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