Ammonium Chloride → 7-bromo-1H,2H,3H,5H-pyrido[2,3-e][1,4]oxazepine

HRID 712629Notes

Reaction equation

HRID 712629 reaction equation
[Br:1][C:2]1[CH:13]=[N:12][C:5]2[NH:6][C:7](=O)[CH2:8][O:9][CH2:10][C:4]=2[CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-].C([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:13]=[N:12][C:5]2[NH:6][CH2:7][CH2:8][O:9][CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 159260057-bromo-1H,2H,3H,5H-pyrido(2,3-e)(1,4)oxazepin-2-one

Product 1

HCID 593328677-bromo-1H,2H,3H,5H-pyrido[2,3-e][1,4]oxazepineYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-5,9-dihydro-6-oxa-1,9-diaza-benzocyclohepten-8-one (205 mg, 0.84 mmol) and sodium borohydride (160 mg, 4.2 mmol) are dissolved in 1.0 mL of THF and the mixture is cooled down to 0° C. Neat BF3 Et2O (0.74 mL, 5.9 mmol) is added dropwise and the mixture is stirred for 3 hr at room temperature. Then saturated aqueous NH4Cl solution (15 mL) is added carefully and the mixture is further basified by adding solid NaHCO3. The mixture is then extracted with EtOAc (3×35 mL). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 78 mg of 3-bromo-5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocycloheptene

Workup

  1. extractionThe mixture is then extracted with EtOAc (3×35 mL)
  2. concentrationconcentrated
  3. customto give the crude product
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-bbd16faf5943409c83dfd08a505cfe02
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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