Nitrogen → HCID 66928958, compound

HRID 2064975Notes

Reaction equation

HRID 2064975 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH2:15]OS(C)(=O)=O)[CH:12]=[N:13][CH:14]=2)[O:8][CH2:7][CH2:6][O:5]1.[N+:21]([C:24]1[CH:25]=[N:26][NH:27][CH:28]=1)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+].[I-]>CC(C)=O>[CH3:3][C:4]1([C:9]2[CH:14]=[N:13][CH:12]=[C:11]([CH2:15][N:26]3[CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:28]=[N:27]3)[CH:10]=2)[O:5][CH2:6][CH2:7][O:8]1

Participants

7

Reactant 5

HCID 947Nitrogen2×HCID 11430Potassium CarbonateHCID 163764-nitro-1H-pyrazoleHCID 30165Iodide IonHCID 86650889HCID 86650889, compound

Product 1

HCID 66928958HCID 66928958, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methanesulfonic acid 5-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-3-ylmethyl ester (271 mg, 0.99 mmol) in acetone (6.0 mL) was added, under inert atmosphere (N2) to a solution of 4-nitro-1H-pyrazole (126 mg, 0.99 mmol) in acetone (6.0 mL). K2CO3 (691 mg, 4.95 mmol) followed by TBA iodide (64 mg, 0.20 mmol) were added to the reaction mixture, which was stirred at rt for 5 h. The solvent was removed under reduced pressure. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (10:1 to 2:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.1. LC-MS-conditions 02: tR=0.74 min; [M+H]+=291.11.

Workup

  1. additionwere added to the reaction mixture, which
  2. customThe solvent was removed under reduced pressure
  3. additionWater (10 mL) and EA (10 mL) were added
  4. extractionThe aq. layer was extracted with EA (10 mL)
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (10:1 to 2:1 hept-EA)

Sources & evidence

ORD record
ord-3f878139948a4d61a9d22f7f3f14102a
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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