Ammonium Chloride → 10-Bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

HRID 886035Notes

Reaction equation

HRID 886035 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13](I)[N:14]=[C:7]3[C:6]=2[CH:16]=1.C([Mg]Br)C.[NH4+].[Cl-]>C1COCC1.C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[CH:13][N:14]=[C:7]3[C:6]=2[CH:16]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5820440710-Bromo-2-iodo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepineHCID 178418443HCID 178418443, compound

Product 1

HCID 5820473910-Bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10-bromo-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (9 g, 20 mmol) in THF (40 mL) was added Ethylmagnesium bromide in Ethyl ether (22 mL) at −20° C. The mixture was allowed to warm to room temperature and in one and half hour the completion was showed by LCMS. The reaction mixture was poured into 10% NH4Cl and extracted by EtOAc. Organic layer was washed by brine, dried by MgSO4 and concentrated. The crude was purified by Isco chromatography to afford 10-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine. LC/MS (ESI+): m/z 265 (M+H).

Workup

  1. extractionextracted by EtOAc
  2. washOrganic layer was washed by brine
  3. dry with materialdried by MgSO4
  4. concentrationconcentrated
  5. customThe crude was purified by Isco chromatography

Sources & evidence

ORD record
ord-850abbe392214bf29f2fe6ad9ca35ce6
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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