Potassium Carbonate → 3-[(1S)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-ethynyl-2-pyridinamine

HRID 1845897Notes

Reaction equation

HRID 1845897 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@@H:10]([O:12][C:13]1[C:14]([NH2:25])=[N:15][CH:16]=[C:17]([C:19]#[C:20][Si](C)(C)C)[CH:18]=1)[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@@H:10]([O:12][C:13]1[C:14]([NH2:25])=[N:15][CH:16]=[C:17]([C:19]#[CH:20])[CH:18]=1)[CH3:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 89708471HCID 89708471, compound

Product 1

HCID 897084843-[(1S)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-ethynyl-2-pyridinamineYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(2-(trimethylsilyl)ethynyl)-2-aminopyridine (10.6 g, 26.7 mmol) was dissolved in methanol (50 mL), potassium carbonate (7.38 g, 53.4 mmol) was added, and the reaction was stirred overnight at room temperature. TLC test showed that the raw materials were completely reacted. The reaction liquid was concentrated under reduced pressure, extracted with ethyl acetate; the organic layer was washed with water and saturated sodium chloride solution successively, dried over anhydrous sodium sulfate, concentrated; the residue was purified via silica gel column chromatography [petroleum ether:ethyl acetate=3:1 (v:v)] to yield the target product as yellow solid (8.2 g, yield: 94%).

Workup

  1. customwere completely reacted
  2. customThe reaction liquid
  3. concentrationwas concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated sodium chloride solution successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customthe residue was purified via silica gel column chromatography [petroleum ether:ethyl acetate=3:1 (v:v)]

Sources & evidence

ORD record
ord-7c16eb2099e545f586f3b258ba20ce47
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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