HCID 90025094, compound → HCID 90025509, compound

HRID 1050925Notes

Reaction equation

HRID 1050925 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[C:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)(=[O:3])[CH3:2]>C1(C)C=CC=CC=1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:11]=[CH:12]\[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 90025094HCID 90025094, compound

Product 1

HCID 90025509HCID 90025509, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 1140TolueneSolvent

Procedure

In an autoclave, 2-(quinolin-2-ylethynyl)phenyl acetate (0.40 g, 1.4 mmol, 1.0 eq.) was dissolved in degassed toluene (15 mL). Lindlar catalyst (5% Pd on CaCO3, 80 mg) was added and the vessel was sealed. The mixture was hydrogenated under 4 bar pressure for 9 h at r.t. The mixture was filtered through a pad of Celite to remove the Pd catalyst and concentrated under reduced pressure which gave the crude product. The product was purified by column chromatography (SiO2, 98.75:1:0.25 dichloromethane-methanol-ammonia) which yielded the product (0.12 g, 30% yield) as a tan solid.

Workup

  1. customthe vessel was sealed
  2. filtrationThe mixture was filtered through a pad of Celite
  3. customto remove the Pd catalyst
  4. concentrationconcentrated under reduced pressure which
  5. customgave the crude product
  6. customThe product was purified by column chromatography (SiO2, 98.75:1:0.25 dichloromethane-methanol-ammonia) which

Sources & evidence

ORD record
ord-2a421cb45c80498bbc298bec56fa84d7
Source dataset
uspto-grants-2016_07
Patent number
US09388138B2

Reaction notes

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