Sodium Carbonate → 4-(2-ethylphenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone

HRID 44201

反応式

HRID 44201 の反応式
Cl[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH3:13]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27749384-Chloro-5-methoxy-2-methyl-2,3-dihydropyridazin-3-oneHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 574373174-(2-ethylphenyl)-5-methoxy-2-methyl-3(2H)-pyridazinone収率 92%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回

実験手順

To a mixture of 2.516 g of 4-chloro-5-methoxy-2-methyl-3 (2H)-pyridazinone, 2.575 g of 2-ethylphenylboronic acid and 3.333 g of sodium carbonate were added 30 mL of 1,4-dioxane and 20 mL of water. To the mixture were added 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis(triphenylphosphine)palladium, and then under a nitrogen atmosphere, the resulting mixture was stirred and heated under reflux for 17 hours. After cooling, 50 mL of water was added to the reaction mixture, which was extracted with 100 mL of ethyl acetate and then 30 mL of ethyl acetate. The extracts were combined, washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The solid obtained was washed with a mixed solvent of ethyl acetate and hexane (1:2) to yield 3.238 g of the title compound as yellow crystals.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 17 hours
  3. temperatureAfter cooling
  4. extractionwas extracted with 100 mL of ethyl acetate
  5. washwashed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe solid obtained
  9. washwas washed with a mixed solvent of ethyl acetate and hexane (1:2)

出典と根拠

ORDレコード
ord-2b623f1378b44c2bbd7832ddf0ef79d5
出典データセット
uspto-grants-2013_09
特許番号
US08541414B2

関連ノート

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