Dichloromethane → HCID 178510924, compound

HRID 2289993Notes

Reaction equation

HRID 2289993 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](/[CH:21]=[CH:22]/[C:23]#[N:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.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]([CH2:21][CH2:22][C:23]#[N:24])=[CH:15][C:14]=3[F:25])=[O:9])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 178510923HCID 178510923, compound

Product 1

HCID 178510924HCID 178510924, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(4-chlorobenzyl)-6-[(E)-2-cyanoethenyl]-8-fluoro-4-hydroxy-3-quinolinecarboxamide from Example No. 133 (0.13 g) and Et3N in 50 mL 3:1 CH2Cl2 :MeOH was added 10% Pd/C (0.040 g). The reaction was placed under hydrogen balloon atmosphere for 4 hours. The reaction was filtered over Celite, the filter cake rinsed thoroughly with methanol, and the filtrate concentrated under reduced pressure to give a yellow solid. The solid was recrystallized with CH2Cl2 /MeOH/hexanes to give the desired product as an off-white solid (0.084 g, 63%).

Workup

  1. customfor 4 hours
  2. filtrationThe reaction was filtered over Celite
  3. washthe filter cake rinsed thoroughly with methanol
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto give a yellow solid
  6. customThe solid was recrystallized with CH2Cl2 /MeOH/hexanes

Sources & evidence

ORD record
ord-13316699387e49cd9499183264ba376b
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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