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

HRID 2044255Notes

Reaction equation

HRID 2044255 reaction equation
C([Mg]Br)C.[I:5][C:6]1[N:7]=[C:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:13]=3[O:12][CH2:11][CH2:10][N:9]2[C:23]=1I.[NH4+].[Cl-]>C(OCC)C.C1COCC1>[I:5][C:6]1[N:7]=[C:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:13]=3[O:12][CH2:11][CH2:10][N:9]2[CH:23]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 67050758HCID 67050758, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 58204516Methyl 2-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-9-carboxylateYield 86%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Fresh ethyl magnesium bromide in ethyl ether (3.0 M 1.1 mL) was added dropwise to a suspension of methyl 2,3-diiodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate (1.1 g, 2.2 mmol) in THF at −15° C. The mixture was stirred and monitored using LC/MS. After 1 hour, there was no remaining starting material and the reaction was poured into sat. NH4Cl and extracted with EtOAc. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated. At the end of this process, 0.7 g (80%) of methyl 2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate was obtained.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ee24baf4474542e0979df93c984f28a7
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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