m-Chloroperbenzoic acid → 1-(2-Butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine-5-oxide

HRID 1107792Notes

Reaction equation

HRID 1107792 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([N:16]1[C:20]2=[C:21]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[N:22]=[N:23][CH:24]=[C:19]2[C:18]([CH3:34])=[C:17]1[CH3:35])[CH:13]=[CH:14][CH3:15]>ClCCl>[CH2:12]([N:16]1[C:20]2=[C:21]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[N:22]=[N+:23]([O-:6])[CH:24]=[C:19]2[C:18]([CH3:34])=[C:17]1[CH3:35])[CH:13]=[CH:14][CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 539969541-(2-Butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine

Product 1

HCID 541608291-(2-Butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine-5-oxideYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.72 g (0.0029 mole) of m-chloroperoxybenzoic acid (purity: 700%) in 20 ml of dichloromethane was added to a solution of 0.72 g (0.0029 mole) of 1-(2-butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine in 70 ml of dichloromethane at room temperature and the resulting mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was washed three times with 40 ml each of a saturated aqueous solution of sodium hydrogencarbonate. The dichloromethane layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 100:1 to 100:4 mixture of chloroform and methanol as an eluent to give crystals, which were washed with a mixture of ether and hexane to give 0.63 g of the title compound (cis/trans=27/73) as a pale yellow powder.

Workup

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed three times with 40 ml each of a saturated aqueous solution of sodium hydrogencarbonate
  3. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel using a 100:1
  6. additionto 100:4 mixture of chloroform and methanol as an eluent
  7. customto give crystals, which
  8. washwere washed with a mixture of ether and hexane

Sources & evidence

ORD record
ord-60556b7bbcfe4d45816913c305f9d3e7
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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