Methyl iodide → (Z)-8-bromo-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 718079Notes

Reaction equation

HRID 718079 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:19]=1)[NH:7][C:8](=[O:18])[CH2:9][N:10]=[C:11]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:19]=1)[N:7]([CH3:22])[C:8](=[O:18])[CH2:9][N:10]=[C:11]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59783468(Z)-8-bromo-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

Product 1

HCID 59783784(Z)-8-bromo-1-methyl-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-oneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Title compound 354 (3.1 g, 11.8 mmol), sodium hydride (565 mg, 14.14 mmol) and methyliodide (0.88 mL, 14.14 mmol) were stirred together in DMF (60 mL) at room temperature for 6 hours. DMF was removed and the residue was partitioned in EtOAc and water. The organic layer was dried, filtered and evaporated. The crude product was purified by flash chromatography (3:1 to 1:2 hexane:ethyl acetate) to afford title compound 357 (2.3 g, 60%) as a white solid.

Workup

  1. customDMF was removed
  2. customthe residue was partitioned in EtOAc
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (3:1 to 1:2 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6bafc14a28d44c55adb1d05e4e83e368
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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