Potassium Carbonate → 1-(2-Azidoethyl)-3-methoxypyridine-2-one

HRID 539534Notes

Reaction equation

HRID 539534 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CS(O[CH2:15][CH2:16][N:17]=[N+:18]=[N-:19])(=O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[N:17]([CH2:16][CH2:15][N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 887313-Methoxy-2-pyridoneHCID 112751972-Azidoethyl methanesulfonate

Product 1

HCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-oneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-methoxypyridine-2-one (0.40 g, 3.20 mmol), 156a (0.79 g, 4.80 mmol), and K2CO3 (1.32 g, 9.60 mmol) stirred overnight in THF at reflux temperature. Reaction mixture was cooled down to room temperature. Reaction mixture was partitioned between CH2Cl2 (60 mL) and water (50 mL). Organic layer washed with water (2×35 mL), brine (1×30 mL). Organic layer dried on Na2SO4 and evaporated in vacuo. Crude product was purified by flash chromatography with stepwise gradient of CH2Cl2 and acetone (max 15%) to give 0.34 mg of 157a (55%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 6.77 (dd, J=6.9, 1.6 Hz, 1H), 6.48 (dd, J=7.5, 1.6 Hz, 1H), 5.96 (m, 1H), 3.91 (m, 2H), 3.62 (s, 3H), 3.52 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.39, 149.41, 128.61, 112.16, 104.37, 55.36, 49.00, 48.91. HRMS (EI) calcd for C8H10N4O2 [M]+ 194.0804. found 194.0816.

Workup

  1. temperatureat reflux temperature
  2. customReaction mixture
  3. customReaction mixture
  4. customwas partitioned between CH2Cl2 (60 mL) and water (50 mL)
  5. washOrganic layer washed with water (2×35 mL), brine (1×30 mL)
  6. customOrganic layer dried on Na2SO4
  7. customevaporated in vacuo
  8. customCrude product was purified by flash chromatography with stepwise gradient of CH2Cl2 and acetone (max 15%)

Sources & evidence

ORD record
ord-2cdb65e1812e440cb74feba4164ae8ca
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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