HCID 68802619, compound → HCID 68802799, compound

HRID 2250602Notes

Reaction equation

HRID 2250602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([C:22]([CH:25]=[CH2:26])=[CH:23][CH:24]=3)[N:11]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:13]=2[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][CH:3]=1>[Pd].C(O)C>[CH2:25]([C:22]1[N:10]2[N:11]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:9]2=[CH:24][CH:23]=1)[CH3:26]

Participants

4

Reactant 1

HCID 68802619HCID 68802619, compound

Product 1

HCID 68802799HCID 68802799, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst3×HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-(4-fluorophenyl)-2-isopropyl-7-vinylpyrrolo[1,2-b]pyridazine-3-carboxylate (8.9 g) and 10% palladium on carbon (900 mg) in ethanol (180 mL) was stirred under hydrogen atomosphere (3.5 atm) at ambient temperature. After 10 hours, the mixture was stood overnight. To the mixture was added 10% palladium on carbon (900 mg) and was stirred under hydrogen atomosphere (35 atm) at ambient temperature. After 12 hours, the mixture was stood overnight. To the mixture was added 10% palladium on carbon (900 mg) and was stirred under hydrogen atomosphere (35 atm) at ambient temperature for 8 hours. The mixture was filtered through Celite. The filtrate was concentrated in vacuo to give ethyl 7-ethyl-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazine-3-carboxylate as an yellow oil (9.0 g, 100.5%).

Workup

  1. waitthe mixture was stood overnight
  2. stirringwas stirred under hydrogen atomosphere (35 atm) at ambient temperature
  3. waitAfter 12 hours
  4. waitthe mixture was stood overnight
  5. stirringwas stirred under hydrogen atomosphere (35 atm) at ambient temperature for 8 hours
  6. filtrationThe mixture was filtered through Celite
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a1d53058e1c346cd817f25b6cc7cbf58
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

Loading…