Methanol → HCID 178494889, compound

HRID 2289966Notes

Reaction equation

HRID 2289966 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][CH2:23][O:24][CH3:25])=[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][CH2:23][O:24][CH3:25])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6326AcetyleneHCID 178494888HCID 178494888, compound

Product 1

HCID 178494889HCID 178494889, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the title compound of Example 95 (0.113 g) and Pd/C (10%, 22.6 mg) is dissolved in 3:1 CH2Cl2 :MeOH. The reaction mixture is placed under the Parr hydrogenator at 25 psi H2 and monitored with the OAMS for complete reduction of the acetylene. The reaction is complete in 1 hr and is filtered over celite. The filtrate is condensed to obtain a white solid. The product is recrystallized with EtOAc/hexanes to yield 32.0 mg of the desired product.

Workup

  1. filtrationis filtered over celite
  2. customcondensed
  3. customto obtain a white solid
  4. customThe product is recrystallized with EtOAc/hexanes

Sources & evidence

ORD record
ord-553e07b2e29b4ba4b8496dd09b6731d2
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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