Tetrahydrofuran → HCID 58204465, compound

HRID 1799921Notes

Reaction equation

HRID 1799921 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[N:7]([C:11](I)=[C:12]([I:14])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.O1CCCC1.C[Mg]Br>CCOCC.[Cl-].[NH4+]>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([I:14])[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 582049149-Fluoro-5,6-dihydro-2,3-diiodoimidazo[1,2-d][1,4]benzoxazepineHCID 178418573HCID 178418573, compound

Product 1

HCID 58204465HCID 58204465, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

9-fluoro-2,3-diiodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (1.24 g, 2.74 mmol) was dissolved in tetrahydrofuran (25 mL, 310 mmol) and cooled to −78° C. in a dry ice/acetone bath. Added 3.0 Methylmagnesium bromide in ether (1.37 mL and allowed the reaction to warm up to −40° C. and stir for 4 hours. Complete by LCMS. Diluted with 100 mL of saturated ammonium chloride and extracted with ethyl acetate. Dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography on the ISCO 0-40% ethyl acetate in hexanes to give 9-fluoro-2-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (0.794 g, 88% yield)

Workup

  1. customthe reaction
  2. temperatureto warm up to −40° C.
  3. extractionextracted with ethyl acetate
  4. dry with materialDried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on the ISCO 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ddaa375f31894f7c8c869057e8f267ce
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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