Triphenylphosphine → HCID 68014807, compound

HRID 1747773Notes

Reaction equation

HRID 1747773 reaction equation
O[CH2:2][C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[N:7]=[C:6]([C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[CH:18][CH:17]=2)[C:5](=[O:27])[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1COCC1>[C:21]1([N:20]2[C:16]([C:6]3[C:5](=[O:27])[CH:4]=[C:3]4[CH2:2][O:15][C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=5[N:8]4[N:7]=3)=[CH:17][CH:18]=[N:19]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 89586214HCID 89586214, compoundHCID 178459888HCID 178459888, compound

Product 1

HCID 68014807HCID 68014807, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-(Hydroxymethyl)-1-(2-hydroxyphenyl)-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (190 mg) was dissolved in toluene (2 mL) and THF (3 mL), triphenylphosphine (202 mg) and 1.9M DIAD toluene solution (410 μL) were added at 0° C., and the reaction mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (130 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ce7e38dc14fb4293b4401e6aa7a58f0c
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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