Potassium Carbonate → 3-Ethynyl-5-fluoropyridin-2-amine

HRID 2382124Notes

Reaction equation

HRID 2382124 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][Si](C)(C)C)[C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:9]([C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([F:1])[CH:3]=1)#[CH:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 597068495-Fluoro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 552886203-Ethynyl-5-fluoropyridin-2-amineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-fluoro-3-trimethylsilanylethynyl-pyridin-2-ylamine (3.2 g, 15.4 mmol) in MeOH (77 mL) and K2CO3 (11 g, 7.7 mmol) is stirred at rt for 0.5 h. The mixture is filtered through Celite and concentrated. The residue is purified by silica gel chromatography eluting with 15%-55% EtOAc in heptane to afford 3-ethynyl-5-fluoro-pyridin-2-ylamine (1.55 g, 74%). MS: 137 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.94 (d, 1H), 7.35 (m, 1H), 4.91 (s, NH2, 2H), 3.44 (s, 1H).

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationconcentrated
  3. customThe residue is purified by silica gel chromatography
  4. washeluting with 15%-55% EtOAc in heptane

Sources & evidence

ORD record
ord-98e80b4c55404c2189b4b81ec651e5cd
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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