Ethanol → HCID 66602913, compound

HRID 2097507Notes

Reaction equation

HRID 2097507 reaction equation
[CH2:1]([OH:3])[CH3:2].[Br:4][C:5]1[N:14]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]2[CH:9]=[N:10][NH:11][C:12](=[O:13])[C:7]=2[C:6]=1[CH2:23]Br.C(O)C.[O-]CC.[Na+]>O>[Br:4][C:5]1[N:14]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]2[CH:9]=[N:10][NH:11][C:12](=[O:13])[C:7]=2[C:6]=1[CH2:23][O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 23706232Ethanol sodium ethoxideHCID 66602907HCID 66602907, compound

Product 1

HCID 66602913HCID 66602913, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 23 ml of ethanol solution containing 1.06 g (2.42 mmol) of 2-bromo-3-bromomethyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 24-(f) was added 3.33 g (9.78 mmol) of 20% sodium ethoxide ethanol solution, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, water 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 concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=2:1→1:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 549 mg of the title compound as a white solid. (Yield: 56%)

Workup

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

Sources & evidence

ORD record
ord-c18b6f3234734141a1c5a580272386b3
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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