Iodoethane → HCID 67264599, compound

HRID 1040672Notes

Reaction equation

HRID 1040672 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12](=[CH:13][CH:14]=1)[CH:11]1[CH2:15][CH:7]2[CH2:8][NH:9][CH2:10]1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH3:23]>CC(C)=O>[CH2:22]([N:9]1[CH2:8][CH:7]2[CH2:15][CH:11]([C:12]3[C:6]2=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=3)[CH2:10]1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 9816191HCID 9816191, compound

Product 1

HCID 67264599HCID 67264599, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-nitro-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (300 mg, 1.47 mmol) (prepared using the procedure detailed in J. Med Chem, 2005, 48, 3474-3477) in 5 ml acetone was added potassium carbonate (609 mg, 4.41 mmol) and then ethyl iodide (423 μl, 5.29 mmol). The solution was allowed to stir overnight. The reaction was evaporated under reduced pressure and partitioned between water and EtOAc. The water layer was extracted with 2×10 ml portions of EtOAc and the combined organics dried over magnesium sulfate, filtered and evaporated. The resulting brown oil was chromatographed on a 12 g Isco column using a gradient of 0-10% methanol in methylene chloride to yield 10-ethyl-4-nitro-10-aza-tricyclo[6.3.1.0*2,7*]dodeca-2,4,6-triene (280 mg, 82%) as a brown oil. 1H-NMR (CDCl3) δ 8.07 (d, J=8.1 Hz, 1H), 7.96 (s, 1H), 7.24 (d, J=8.1 Hz, 1H), 3.17 (dd, J=5.5, 4.8 Hz, 2H), 2.87 (dd, J=5.5, 4.8 Hz, 2H); 2.40-2.20 (m, 5H), 1.75 (d, J=10.6 Hz), 0.85 (d, J=10.6 Hz, 3H).

Workup

  1. customThe reaction was evaporated under reduced pressure
  2. custompartitioned between water and EtOAc
  3. extractionThe water layer was extracted with 2×10 ml portions of EtOAc
  4. dry with materialthe combined organics dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting brown oil was chromatographed on a 12 g Isco column

Sources & evidence

ORD record
ord-073ef2ac0b5a4547834248f1e625c30e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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