Methyl iodide → HCID 117601303, compound

HRID 1773677Notes

Reaction equation

HRID 1773677 reaction equation
[Br:1][C:2]1[C:12]2[CH2:11][CH2:10][CH2:9][C:8](=[O:13])[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:14].[H-].[Na+].[CH3:17]I>CN(C=O)C>[Br:1][C:2]1[C:12]2[CH2:11][CH2:10][CH2:9][C:8](=[O:13])[N:7]([CH3:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117601487HCID 117601487, compound

Product 1

HCID 117601303HCID 117601303, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Bromo-7-methyl-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (100.0 mg, 1.998 mmol) was treated with NaH (18.9 mg, 0.472 mmol, 1.2 equiv) in DMF (3 mL) at 0° C. to room temperature for 30 min. To the mixture was added MeI (111.7 mg, 0.787 mmol, 2 equiv). The mixture was stirred at to room temperature for 1 h The mixture was quenched with water and extracted with EtOAc (30 mL×3). The organic layer was washed with brine (30 mL) and dried over Na2SO4. The solvent was removed under a reduced pressure and the crude product was purified by a silica-gel column chromatography (hexane/EtOAc 87:13 to 50:50) to give 6-bromo-1,7-dimethyl-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one (88.5 mg, 83.9%).

Workup

  1. customwas quenched with water
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under a reduced pressure
  6. customthe crude product was purified by a silica-gel column chromatography (hexane/EtOAc 87:13 to 50:50)

Sources & evidence

ORD record
ord-e6a985eed6414b72be9edbc793f4b93b
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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