Water → 3-Ethynylpyridin-2-amine

HRID 77796Notes

Reaction equation

HRID 77796 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:8]([NH2:13])=[N:9][CH:10]=[CH:11][CH:12]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:6]([C:7]1[C:8]([NH2:13])=[N:9][CH:10]=[CH:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 574756663-((Trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 124225263-Ethynylpyridin-2-amineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-trimethylsilanylethynyl-pyridin-2-ylamine (28.1 g, 148 mmoL) described in Manufacturing Example 1-2-2 in tetrahydrofuran (300 mL) was added tetrabutylammonium fluoride (1 M tetrahydrofuran solution, 20 mL, 20 mmol), which was stirred for 15 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate 4 times. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=1:1 then 1:2) to obtain the title compound (16.4 g, 93.7%).

Workup

  1. extractionwas then extracted with ethyl acetate 4 times
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by silica gel chromatography (heptane

Sources & evidence

ORD record
ord-28557e6571f64d84b8e6524cf1f92b12
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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