3,4-bis(benzyloxy)-6-[(E)-2-(3,5-difluorophenyl)vinyl]pyridazine → HCID 178518833, compound

HRID 1503219Notes

Reaction equation

HRID 1503219 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>[C].[Pd].C(O)C>[F:32][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][C:12]2[CH:13]=[C:14]([OH:15])[C:9](=[O:8])[NH:10][N:11]=2)[CH:30]=[C:29]([F:31])[CH:28]=1

Participants

4

Reactant 1

HCID 1176911593,4-bis(benzyloxy)-6-[(E)-2-(3,5-difluorophenyl)vinyl]pyridazine

Product 1

HCID 178518833HCID 178518833, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10% palladium-carbon (280 mg), ethanol (25 mL) and 3,4-bis(benzyloxy)-6-[(E)-2-(3,5-difluorophenyl)vinyl]pyridazine (710 mg) was stirred under a hydrogen atmosphere at room temperature for 1 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added diethyl ether and the obtained solid was dried under reduced pressure to give 6-[2-(3,5-difluorophenyl)ethyl]-4-hydroxypyridazin-3(2H)-one (140 mg).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the obtained residue was added diethyl ether
  4. customthe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-b1a5dc7e5eee485fbe44f76576352d13
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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