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

HRID 44201

반응식

HRID 44201 반응식
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]

참가 물질

8

반응물 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)

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2b623f1378b44c2bbd7832ddf0ef79d5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541414B2

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