Ammonium Chloride → 9-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

HRID 1629068Notes

Reaction equation

HRID 1629068 reaction equation
C([Mg]Br)C.[Br:5][C:6]1[CH:21]=[CH:20][C:9]2[C:10]3[N:11]([C:15](I)=[C:16]([I:18])[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[Br:5][C:6]1[CH:21]=[CH:20][C:9]2[C:10]3[N:11]([CH:15]=[C:16]([I:18])[N:17]=3)[CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 582047669-Bromo-5,6-dihydro-2,3-diiodoimidazo(1,2-d)(1,4)benzoxazepineHCID 178418443HCID 178418443, compound

Product 1

HCID 582048589-Bromo-2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepineYield 81.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 3.0 M solution of ethylmagnesium bromide in ethyl ether (1.1 mL) was added dropwise to a suspension of 9-bromo-2,3-diiodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (1.1 g, 2.2 mmol) in THF at −15° C. The mixture was stirred and followed by LC/MS. After 1 hour, there is no starting material left and the reaction was poured into sat. NH4Cl and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated. The crude residue was purified by flash column chromatography to provide 9-bromo-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine as white solid (0.7 g).

Workup

  1. waitleft
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-9a5ad49d40a54053b15e54e138e018c2
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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