Pyridine → HCID 86667166, compound

HRID 2367939Notes

Reaction equation

HRID 2367939 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([OH:11])[CH2:9][CH2:8][CH2:7][C@@H:6]1[N:12]=[N+:13]=[N-:14])(=[O:3])[CH3:2].N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@@H:10]([OH:11])[CH2:9][CH2:8][CH2:7][C@@H:6]1[N:12]=[N+:13]=[N-:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86667164HCID 86667164, compound

Product 1

HCID 86667166HCID 86667166, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 4 (416 mg, 2.09 mmol) and pyridine (506 μL, 6.27 mmol) in CH2Cl2 (10 mL), Tf2O (421 μL, 2.51 mmol) was dropwise added at −10° C. The mixture was left to react for 10 min when it was diluted (CH2Cl2), washed (HCl(aq) 5%, NaHCO3(aq) sat, brine), dried (MgSO4), filtered and concentrated. The crude was then dissolved in DMF (20 mL). Bu4NNO2 (1810 mg, 6.27 mmol) was added and the mixture was heated to 50° C. After 1 h the mixture was cooled to room temperature. and concentrated. Purification was made by flash chromatography using EtOAc:n-heptan (1:1) as eluent. The reaction yielded 64% of 8. 1H-NMR (CDCl3) 4.79 (dd, J=4.78, 9.75 Hz, 1 H), 4.17 (m, 1 H), 3.83 (ddd, J=4.58, 9.84, 11.29 Hz, 1 H), 2.18 (s, 3 H), 2.00-2.10 (m, 1 H), 1.85-1.95 (m, 1 H), 1.70-1.80 (m, 1 H), 1.50-1.65 (m, 2 H), 1.30-1.45 (m, 1 H)

Workup

  1. waitThe mixture was left
  2. customto react for 10 min when it
  3. washwashed (HCl(aq) 5%, NaHCO3(aq) sat, brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude was then dissolved in DMF (20 mL)
  8. additionBu4NNO2 (1810 mg, 6.27 mmol) was added
  9. temperatureAfter 1 h the mixture was cooled to room temperature
  10. concentrationand concentrated
  11. customPurification

Sources & evidence

ORD record
ord-0a9156c3b81246e48358730e00cf2a58
Source dataset
uspto-grants-2014_04
Patent number
US08703720B2

Reaction notes

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