Triphenylphosphine → 3-(1-methyl-1H-pyrazol-5-yl)-1-phenyl-5-(2-quinolin-2-ylethoxy)pyridazin-4(1H)-one

HRID 333743Notes

Reaction equation

HRID 333743 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:36][C:37]1[C:38](=[O:55])[C:39]([C:49]2[N:53]([CH3:54])[N:52]=[CH:51][CH:50]=2)=[N:40][N:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:42]=1.[N:56]1[C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[CH:59]=[CH:58][C:57]=1[CH2:66][CH2:67]O>C1(C)C=CC=CC=1>[CH3:54][N:53]1[C:49]([C:39]2[C:38](=[O:55])[C:37]([O:36][CH2:67][CH2:66][C:57]3[CH:58]=[CH:59][C:60]4[C:65](=[CH:64][CH:63]=[CH:62][CH:61]=4)[N:56]=3)=[CH:42][N:41]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:40]=2)=[CH:50][CH:51]=[N:52]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 895867585-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one

Product 1

HCID 895862523-(1-methyl-1H-pyrazol-5-yl)-1-phenyl-5-(2-quinolin-2-ylethoxy)pyridazin-4(1H)-oneYield 70.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (20 mL) was added to di-tert-butyl diazene-1,2-dicarboxylate (345 mg), triphenylphosphine (459 mg) and the mixture was stirred at room temperature for 10 min. Then, 5-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one (268 mg), and further, 2-quinolin-2-ylethanol (260 mg) were added, and the mixture was stirred at room temperature for 64 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol). A fraction containing the title compound was again purified by NH silica gel column chromatography (hexane/ethyl acetate) and crystallized from hexane/ethyl acetate to give the title compound (297 mg) as white needles.

Workup

  1. stirringthe mixture was stirred at room temperature for 64 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  4. additionA fraction containing the title compound
  5. customwas again purified by NH silica gel column chromatography (hexane/ethyl acetate)
  6. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-07eb13a060ba4f03b19331bc7d10dfab
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

Loading…