Iodine → 5,6,7,9-Tetrahydro-7-iodo-8H-pyrido[2,3-b]azepin-8-one

HRID 481762Notes

Reaction equation

HRID 481762 reaction equation
[N:1]1[C:6]2[NH:7][C:8](=[O:12])[CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.CN(C)CCN(C)C.C[Si]([I:25])(C)C.II.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[I:25][CH:9]1[C:8](=[O:12])[NH:7][C:6]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 807Iodine2×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 24437Sodium SulfiteHCID 85247Trimethylsilyl iodideHCID 124131746,7-Dihydro-5H-pyrido[2,3-b]azepin-8(9H)-one

Product 1

HCID 190670745,6,7,9-Tetrahydro-7-iodo-8H-pyrido[2,3-b]azepin-8-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 300 mg of 5,6,7,9-tetrahydro-8H-pyrido[2,3-b]azepin-8-one in 3 mL of dichloromethane at 0° C. was added 0.84 mL of N,N,N',N'-tetramethylethylenediamine (TMEDA) and 0.78 mL of trimethylsilyl iodide. After 30 min, 720 mg of solid iodine was added in one portion. The reaction mixture was stirred at 0° C. an additional 40 min before dichloromethane and excess aqueous sodium sulfite was added to reduce the excess iodine. The mixture was extracted with dichloromethane and the extracts were evaporated to yield 550 mg of the crude product. Flash chromatographic separation on silica gel with ethyl acetate gave 333 mg of purified product characterized by its NMR and mass spectra.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with dichloromethane
  3. customthe extracts were evaporated
  4. customto yield 550 mg of the crude product
  5. customFlash chromatographic separation on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-9240f328a1de445cb0ba8186cd63f066
Source dataset
uspto-grants-1998_08
Patent number
US05789587

Reaction notes

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