Methanol → HCID 178522904, compound

HRID 2290005Notes

Reaction equation

HRID 2290005 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][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][CH2:23][CH2:24][CH2:25][OH:26])=[CH:15][C:14]=3[F:27])=[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][CH2:23][CH2:24][CH2:25][OH:26])=[CH:15][C:14]=3[F:27])=[O:9])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178522903HCID 178522903, compound

Product 1

HCID 178522904HCID 178522904, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(5-hydroxy-1-pentynyl)-3-quinolinecarboxamide from Example 107 (230 mg) and Pd/C (10%, 46.0 mg) is dissolved in 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 38 psi H2 and monitored by mass spectroscopy for complete reduction of the acetylene. The reaction is complete in 11/2 h and filtered over celite to remove the palladium. The filtrate is condensed to afford 129.3 mg (56%) of the title compound as a white solid.

Workup

  1. custom2 h
  2. filtrationfiltered over celite
  3. customto remove the palladium
  4. customcondensed

Sources & evidence

ORD record
ord-a22f56320fec4271b514a1b1daa57e8d
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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