Diethyl Ether → Methyl 10-iodo-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylate

HRID 886012Notes

Reaction equation

HRID 886012 reaction equation
C([Mg]Br)C.C(OCC)C.I[C:11]1[N:12]=[C:13]2[CH2:19][CH2:18][O:17][C:16]3[CH:20]=[C:21]([C:24]([O:26][CH3:27])=[O:25])[CH:22]=[N:23][C:15]=3[N:14]2[C:28]=1[I:29].O1CCCC1>[NH4+].[Cl-]>[I:29][C:28]1[N:14]2[C:15]3[N:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][C:16]=3[O:17][CH2:18][CH2:19][C:13]2=[N:12][CH:11]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 58205031Methyl 9,10-diiodo-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylateHCID 178418443HCID 178418443, compound

Product 1

HCID 86652295Methyl 10-iodo-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Ethylmagnesium bromide in ethyl ether (3.0 M, 0.104 mL, 0.31 mmol)) was added dropwise to a suspension of methyl 9,10-diiodo-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-3-carboxylate (130 mg, 0.26 mmol) in Tetrahydrofuran (5.0 mL, 62 mmol) at −15° C. The mixture was stirred for 15-20 min (a completion was monitored by LCMS), pour into 20 ml of sat. aq. NH4Cl and extracted with ethyl acetate. The organic extracts were washed with water (2×20 ml), brine, dried over MgSO4 and concentrated in vacuum. Weight 92 mg (94%). MS (ESI+): 372.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water (2×20 ml), brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-441c1ea6da2f41f4a9dea878ad3b1f3c
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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