HCID 69514008, compound → HCID 69347479, compound

HRID 855266Notes

Reaction equation

HRID 855266 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([C:11]#[C:12][CH2:13][CH3:14])[C:5]=1[NH2:15]>CC#N.[Pd](Cl)Cl>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]2[C:5]=1[NH:15][C:12]([CH2:13][CH3:14])=[CH:11]2)=[O:16]

Participants

4

Reactant 1

HCID 69514008HCID 69514008, compound

Product 1

HCID 69347479HCID 69347479, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-amino-3-but-1-ynyl-5-chlorobenzoic acid methyl ester (82 mg, 0.35 mmol) in MeCN was added palladium(II)chloride (3 mg, 0.02 mmol) and the reaction mixture was immersed into a preheated oil bath and refluxed for 20 min. The solvent was removed in vacuo and the residue was dissolved in ether and filtered through a short pad of silica. The resulting residue was purified by flash column chromatography (1:9 EtOAc:cyclohexane) to give the desired product (78 mg, 95%) as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ 9.56 (br s, 1H), 7.74 (s, 1H), 7.67 (s, 1H), 6.22 (s, 1H), 3.97 (s, 3H), 2.82 (q, J=7.5 Hz, 2H), 1.38 (t, J=7.5 Hz, 3H).

Workup

  1. customthe reaction mixture was immersed into a preheated oil bath
  2. temperaturerefluxed for 20 min
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ether
  5. filtrationfiltered through a short pad of silica
  6. customThe resulting residue was purified by flash column chromatography (1:9 EtOAc:cyclohexane)

Sources & evidence

ORD record
ord-99cb825e6cbd40eb8e373fb0e68091e9
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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