Triphenylphosphine → HCID 19700655, compound

HRID 861976Notes

Reaction equation

HRID 861976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:19][O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27]O)=[CH:23][CH:22]=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>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[N:10]([CH2:27][C:24]3[CH:25]=[N:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 12259941(6-Methoxypyridin-3-yl)methanolHCID 19700680HCID 19700680, compound

Product 1

HCID 19700655HCID 19700655, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8-(3-chlorophenyl)pyrido-[2,3-d]pyridazin-5-one (0.515 g, 2.0 moles), 6-methoxy-3-hydroxymethyl pyridine (0,306g, 2.2 moles) and triphenylphosphine (0.792 g, 3.0 moles) in THF (50 mL) was added diisopropylazodicarboxylate (0.6mL, 3.0 moles). The reaction mixture was stirred for 18 hours at room temperature. The solvent was removed and the product was purified by chromatography (ethyl acetate/hexane 2:3) and crystallized from methanol to yield 0.588g of 8-(3-chlorophenyl)-6-(6-methoxy-3-pyridylmethyl)pyrido[2,3-d]-pyridazin-5-one, mp 145° C.

Workup

  1. customThe solvent was removed
  2. customthe product was purified by chromatography (ethyl acetate/hexane 2:3)
  3. customcrystallized from methanol

Sources & evidence

ORD record
ord-26eb9e4e9e024c838b5efe4b4badc1b1
Source dataset
uspto-grants-1998_02
Patent number
US05716954

Reaction notes

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