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Methanol → CID 68796711

HRID 449951
Notes
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Reaction equation

HRID 449951 reaction equation
[N+:1](=[C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[N:6][N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[C:4]1=[O:22])=[N-:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.C(=O)(O)[O-].[Na+]>C(#N)C.[Cl-].[Na+].O.O>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:5]1[C:4](=[O:22])[C:3](=[N:1][NH2:2])[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[N:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 178514319HCID 178514319, compound

Product 1

HCID 178514320CID 68796711

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

4-Diazo-2,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one [(Example 18, Step 2) 213 mg, 0.714 mmol] was dissolved in acetonitrile (10 mL) and treated with triphenylphosphine (225 mg, 0.857 mmol, 1.2 equiv). After stirring for 30 minutes at ambient temperature, the mixture was treated with methanol (5 mL) and water (5 mL) and warmed to 60° C. for 1 hour. The mixture was cooled to ambient temperature, poured into brine (50 mL) and sodium bicarbonate (20 mL, aqueous saturated) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 70:30; hexanes:ethyl acetate), providing the titled compound.

Workup

  1. temperaturewarmed to 60° C. for 1 hour
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel gradient chromatography (100:0 to 70:30; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-84de7bfca1c0440e8a5f7fbfa209c390
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486946B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes