Dichloromethane → HCID 178522908, compound

HRID 2289992Notes

Reaction equation

HRID 2289992 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][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][OH:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:4][CH:3]=1.C(Cl)Cl>[Pd].C([O-])([O-])=O.[Ca+2].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][OH:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 178522909HCID 178522909, compound

Product 1

HCID 178522908HCID 178522908, compound

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Example No. 53 (0.24 g) in 60 mL 3:1 CH2Cl2 :MeOH was added a spatula tip of 5% Pd/CaCO3. The reaction was placed under hydrogen balloon atmosphere. After 2 hours, the Pd catalyst was filtered over Celite, new catalyst added to the filtrate and the reaction again placed under a hydrogen balloon. This regeneration of catalyst was repeated 8 times and the reaction monitored by MS until complete. The reaction mixture was filtered over celite and the filter cake washed thoroughly with MeOH and CH2Cl2. The filtrate was concentrated under reduced pressure to give a tan solid which was a 2:1 mixture of desired product and over-reduced material as shown by NMR. This mixture was further purified by HPLC (Cyclobond 2000) to give the desired product (0.072 g, 30%).

Workup

  1. filtrationthe Pd catalyst was filtered over Celite, new catalyst
  2. additionadded to the filtrate
  3. customthe reaction
  4. filtrationThe reaction mixture was filtered over celite
  5. washthe filter cake washed thoroughly with MeOH and CH2Cl2
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto give a tan solid which

Sources & evidence

ORD record
ord-28bb34530cb7486b9580c499a018f18a
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…