Pyridine → HCID 178522905, compound

HRID 2289967Notes

Reaction equation

HRID 2289967 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][CH2:24][OH:25])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.C(Cl)Cl>[Pd].CO>[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](/[CH:21]=[CH:22]\[CH2:23][CH2:24][OH:25])=[CH:15][C:14]=3[F:26])=[O:9])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 178522906HCID 178522906, compound

Product 1

HCID 178522905HCID 178522905, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of the title compound of Example 94 (0.393 g), pyridine (3 mL), and Pd/C (10%, 80.0 mg) in 3:1 CH2Cl2 :MeOH is maintained under an atmosphere of H2 (balloon) for 3 hrs. More Pd/C (10%, 40 mg) is added and the reaction mixture is placed under the Parr hydrogenator at 25 psi H2 for an additional 3 hrs. The reaction mixture is filtered over celite. The filtrate is condensed and then placed under high vac to remove residual pyridine. The crude product is recrystallized with EtOAc/hexanes to afford 0.218g of the desired product as a tan solid.

Workup

  1. filtrationThe reaction mixture is filtered over celite
  2. customcondensed
  3. customto remove residual pyridine
  4. customThe crude product is recrystallized with EtOAc/hexanes

Sources & evidence

ORD record
ord-7733d996a88e4fb79c713e81379b070a
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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