Water → (2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-fluoro-4-hydroxy-phenyl)-methanone

HRID 1943666Notes

Reaction equation

HRID 1943666 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([F:17])[CH:10]=2)=[O:8])[C:3]2[CH:18]=[N:19][CH:20]=[CH:21][C:2]1=2.B(Br)(Br)Br.CCCCCC.O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:17])[CH:10]=2)=[O:8])[C:3]2[CH:18]=[N:19][CH:20]=[CH:21][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8058HexaneHCID 25134Boron tribromideHCID 66936494(2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-fluoro-4-methoxy-phenyl)-methanone

Product 1

HCID 44608072(2,3-Dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-fluoro-4-hydroxy-phenyl)-methanoneYield 31.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a 10 ml flask, (2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-fluoro-4-methoxy-phenyl)-methanone (30 mg, 0.104 mmol) was dissolved in dichloromethane and the mixture was cooled to 0□. 1.0M Boron tribromide dissolved in dichloromethane (1.25 ml, 1.25 mmol) was added thereto and stirred at room temperature for 10 hours. n-hexane and water were added and then filtered to obtain solid. The resulting solid was purified by preparative LC-Mass using 0.05% TFA in acetonitrile and 0.05% TFA in water solvent. The fractions containing the product were collected and adjusted to pH 6 to 7 with saturated solution of sodium hydrogen carbonate. The organic layer was extracted with ethyl acetate. The combined organic layer was evaporated under reduced pressure to obtain the target compound 26 as white solid (9 mg, 28%).

Workup

  1. temperaturethe mixture was cooled to 0□
  2. additionwas added
  3. filtrationfiltered
  4. customto obtain solid
  5. customThe resulting solid was purified by preparative LC-Mass
  6. additionThe fractions containing the product
  7. customwere collected
  8. extractionThe organic layer was extracted with ethyl acetate
  9. customThe combined organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5ecf15f7ce8f4dc9b2c98a6a383871f0
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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