Triphenylphosphine → HCID 23503292, compound

HRID 1835174Notes

Reaction equation

HRID 1835174 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-].C(C1C=CC=C(C(C)(C)C)C=1O)(C)(C)C.[CH3:47][S:48][CH2:49][CH2:50]O.[CH:52]1([CH2:55][C:56]2[C:61]3[S:62][C:63]([CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[C:69]([C:73]([F:76])([F:75])[F:74])[CH:68]=4)=[C:64]([OH:65])[C:60]=3[C:59](=[O:77])[N:58]([CH3:78])[N:57]=2)[CH2:54][CH2:53]1>O1CCCC1>[CH:52]1([CH2:55][C:56]2[C:61]3[S:62][C:63]([CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[C:69]([C:73]([F:76])([F:75])[F:74])[CH:68]=4)=[C:64]([O:65][CH2:50][CH2:49][S:48][CH3:47])[C:60]=3[C:59](=[O:77])[N:58]([CH3:78])[N:57]=2)[CH2:53][CH2:54]1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 314052,6-Di-tert-butylphenolHCID 789252-(Methylthio)ethanolHCID 14357405DiethyldiazodicarboxylateHCID 23503283HCID 23503283, compound

Product 1

HCID 23503292HCID 23503292, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent5×

Procedure

To 5 ml of dry tetrahydrofuran was added 0.64 ml of 1M triphenylphosphine in tetrahydrofuran followed by 0.64 ml of 1M diethyl diazodicarboxylate in tetrahydrofuran and then by 0.64 ml of 1M 2,6-di-t-butylphenol in tetrahydrofuran. This mixture was mixed for 5 minutes and then 1.28 ml of 0.5M 2-(methylthio)ethanol in tetrahydrofuran was added. The solution was then mixed for 5 minutes. 7-Cyclopropylmethyl-3-hydroxy-5-methyl-2-[(3-trifluoromethylphenyl)methyl]thieno[2,3-d]pyridazin-4(5H)-one (248 mg in 1 ml tetrahydrofuran) was added and the solution was mixed periodically over 24 hours. The solution was opened to the air for 18 hours and then purified by chromatography, eluting with an isohexane ethyl acetate gradient, to give the title compound (77 mg).

Workup

  1. additionThis mixture was mixed for 5 minutes
  2. additionThe solution was then mixed for 5 minutes
  3. additionthe solution was mixed periodically over 24 hours
  4. custompurified by chromatography
  5. washeluting with an isohexane ethyl acetate gradient

Sources & evidence

ORD record
ord-84826709835f45428f8b068fbb8d49a2
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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