Sodium Chloride → 2-Chloro-3-phenyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

HRID 2097512Notes

Reaction equation

HRID 2097512 reaction equation
[Cl:1][C:2]1[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2[CH:6]=[N:7][NH:8][C:9](=[O:10])[C:4]=2[C:3]=1I.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>C(O)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:11]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2[CH:6]=[N:7][NH:8][C:9](=[O:10])[C:4]=2[C:3]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 666028262-Chloro-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Product 1

HCID 666029002-Chloro-3-phenyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-oneYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 206 mg (0.484 mmol) of 2-chloro-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 30-(b) were added 71 mg (0.58 mmol) of phenylboronic acid, 54 mg of tetrakistriphenylphosphine palladium, 6 ml of toluene, 4 ml of ethanol and 1 ml of 2M aqueous sodium carbonate solution, the mixture was degassed under reduced pressure and replaced with argon, and the mixture was stirred at 80° C. for 16 hours. After completion of the reaction, a saturated aqueous solution of sodium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer after separation was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; toluene:ethyl acetate=1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 152 mg of the title compound as a pale yellowish solid. (Yield: 84%)

Workup

  1. customthe mixture was degassed under reduced pressure
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer after separation
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionthe fractions containing the desired compound
  8. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-96f54a9b2e6f4a6e89805469e8ea08bf
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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