Pyridine → HCID 18469799, compound

HRID 1636373Notes

Reaction equation

HRID 1636373 reaction equation
[CH3:1][C:2]1([CH3:17])[O:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([NH2:15])=O)=[N:11][CH:12]=2)[CH:4]([CH3:16])[O:3]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:17])[O:6][CH:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:15])=[N:11][CH:12]=2)[CH:4]([CH3:16])[O:3]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 18469798HCID 18469798, compound

Product 1

HCID 18469799HCID 18469799, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 5-(2,2,5-trimethyl-1,3-dioxolan-4-yl)-2-pyridinecarboxamide (16.4 mg, 0.0695 mmol) in 1,4-dioxane (1 ml) were added pyridine (23 ml, 0.278 mmol) and trifluoroacetic anhydride (20 ml, 0.139 mmol) at room temperature. After stirring at room temperature for 1 h, the mixture was diluted with ethyl acetate (20 ml), washed with sat. NaHCO3 (10 ml×2), dried over Na2SO4, and concentrated in vacuo to give a brown syrup. This was purified by preparative TLC [acetone/hexane (1/4, v/v)] to afford 9.7 mg (64%) of 5-(2,2,5-trimethyl-1,3-dioxolan-4-yl)-2-pyridinecarbonitrile as a solid:1H-NMR (270 MHz, CDCl3) δ 8.62 (1 H, d, J=1.8 Hz), 7.80 (1 H, dd, J=1.8 and 8.1 Hz), 7.70 (1 H, d, J=8.1 Hz), 5.25 (1 H, d, J=7.0 Hz), 4.67 (1 H, quit. J=6.6 Hz), 1.64 and 1.48 (each 3H, 2 s), 0.82 (3 H, d, J=6.6 Hz) ppm.

Workup

  1. washwashed with sat. NaHCO3 (10 ml×2)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give a brown syrup
  5. customThis was purified by preparative TLC [acetone/hexane (1/4, v/v)]

Sources & evidence

ORD record
ord-e304946bd8f84854bf06aba7a89f88c9
Source dataset
uspto-grants-2000_03
Patent number
US06034107

Reaction notes

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