Potassium Carbonate → 6-Ethynyl-3-(propan-2-yl)[1,2,4]triazolo[4,3-a]pyridine

HRID 1826706Notes

Reaction equation

HRID 1826706 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([C:13]#[C:14][Si](C)(C)C)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([C:13]#[CH:14])[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22136202HCID 22136202, compound

Product 1

HCID 221362016-Ethynyl-3-(propan-2-yl)[1,2,4]triazolo[4,3-a]pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 250 mL round bottom flask was added 2.5 g (9.71 mmol) of 3-Isopropyl-6-trimethylsilanylethynyl-[1,2,4]triazolo(4,3-a)pyridine, 50 mL of methanol, and 4.03 g (29.1 mmol) of potassium carbonate. This suspension was stirred at room temperature for 2 hours. The reaction mixture was concentrated, and the residue was suspended in 100 mL of water, which was extracted with (2×100 mL) ethyl acetate. The organic extracts were combined, washed with 100 mL of a 1:1 solution of brine and water, dried over magnesium sulfate, filtered, and concentrated to dryness to yield 1.47 grams (82%) of a light brown solid. HPLC tR=3.22 min (93%), LC-MS=186 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionwhich was extracted with (2×100 mL) ethyl acetate
  3. washwashed with 100 mL of a 1:1 solution of brine and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-92d5e20b5167468b940182053beb3704
Source dataset
uspto-grants-2006_05
Patent number
US07053095B2

Reaction notes

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