Butyl vinyl ether → 3-Acetyl-1-benzyloxymethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097499Notes

Reaction equation

HRID 2097499 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]2[CH:15]=[N:16][NH:17][C:18](=[O:19])[C:13]=2[C:12](I)=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:25]C=C)[CH2:22]CC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O>[C:21]([C:12]1[C:13]2[C:18](=[O:19])[NH:17][N:16]=[CH:15][C:14]=2[N:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:11]=1)(=[O:25])[CH3:22]

Participants

6

Reactant 2

HCID 8108Butyl vinyl etherHCID 666030081-Benzyloxymethyl-3-iodo-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666027273-Acetyl-1-benzyloxymethyl-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 40%

Reagents, catalysts & solvents 3

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 43 ml of dehydrated N,N-dimethylformamide solution containing 6.48 g (17.0 mmol) of 1-benzyloxymethyl-3-iodo-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 21-(b) were added 0.19 g (0.46 mmol) of 1,3-bis(diphenylphosphino)propane, 94 mg (0.42 mmol) of palladium acetate and 8.4 g (83.9 mmol) of butyl-vinyl ether, and after degassing under reduced pressure, 4.7 ml of triethylamine was further added to the mixture under nitrogen atmosphere, and the mixture was stirred at 100° C. for 7.5 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, the obtained residue was applied to silica gel column chromatography (Eluent; toluene:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 2.02 g of the title compound as a pale yellowish solid. (Yield: 40%)

Workup

  1. customafter degassing under reduced pressure, 4.7 ml of triethylamine
  2. additionwas further added to the mixture under nitrogen atmosphere
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionthe fractions containing the desired compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-afec8a08fbb64fe599908a67edb95df5
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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