Potassium Carbonate → 3-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-5-ethynyl-2-aminopyridine

HRID 1845884Notes

Reaction equation

HRID 1845884 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([O:14][CH:15]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=2[Cl:25])[CH3:16])[C:10]([NH2:13])=[N:11][CH:12]=1)(C)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[C:6]([C:7]1[CH:8]=[C:9]([O:14][CH:15]([C:17]2[C:22]([Cl:23])=[CH:21][CH:20]=[C:19]([F:24])[C:18]=2[Cl:25])[CH3:16])[C:10]([NH2:13])=[N:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 1234568855-Trimethylsilylethynyl-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine

Product 1

HCID 897084823-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-5-ethynyl-2-aminopyridineYield 69.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-trimethylsilylethynyl-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine (1.5 g, 3.77 mmol) was dissolved in the mixed solvent of THF (10 mL) and MeOH (10 mL), K2CO3 (1.04 g, 7.55 mmol) was added, and the mixture was stirred for 2 h at room temperature. The majority of the solvent was removed under reduced pressure, water (10 mL) was added. The resultant mixture was extracted with ethyl acetate (3×20 mL), the organic phases were combined, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated, the resultant residue was purified via silica gel column chromatography (petroleum ether/ethyl acetate=3:1) to yield 850 mg of the target product as brown solid.

Workup

  1. additionwas added
  2. customThe majority of the solvent was removed under reduced pressure, water (10 mL)
  3. additionwas added
  4. extractionThe resultant mixture was extracted with ethyl acetate (3×20 mL)
  5. washwashed with water and saturated brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customthe resultant residue was purified via silica gel column chromatography (petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ee9b7764988f420a91bef88334ab42fc
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

Loading…