Methanol → HCID 178467738, compound

HRID 2289988Notes

Reaction equation

HRID 2289988 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH:23]([OH:25])[CH3:24])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:4][CH:3]=1.CO.C#C>C(Cl)Cl.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([CH2:21][CH2:22][CH:23]([OH:25])[CH3:24])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178467737HCID 178467737, compound

Product 1

HCID 178467738HCID 178467738, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxy-1-butynyl)-3-quinolinecarboxamide from Example No. 96 (173.7 mg) and Pd/C (10%, 34.7 mg) was dissolved in 3:1 CH2Cl2 :MeOH. The reaction mixture was placed under the Parr hydrogenator and monitored with the OAMS for complete reduction of the acetylene. The reaction was completed in 1 hr and filtered over celite to remove the palladium. The filtrate was condensed to obtain a yellow solid. The crude product was recrystallized with EtOAc/hexanes to yield 123.8 mg (71%) of the desired product as an off-white solid.

Workup

  1. filtrationfiltered over celite
  2. customto remove the palladium
  3. customcondensed
  4. customto obtain a yellow solid
  5. customThe crude product was recrystallized with EtOAc/hexanes

Sources & evidence

ORD record
ord-67e8e1f0c05543b597b14048b3d6e7cf
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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