Tetrahydrofuran → 1-[4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-phenyl]-ethanone

HRID 1943734노트

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HRID 1943734 반응식
O1CCCC1.Br[C:7]1[CH:16]=[N:15][C:10]2[O:11][CH2:12][CH2:13][NH:14][C:9]=2[CH:8]=1.[C:17]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)(=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>O>[NH:14]1[CH2:13][CH2:12][O:11][C:10]2[N:15]=[CH:16][C:7]([C:23]3[CH:24]=[CH:25][C:20]([C:17](=[O:19])[CH3:18])=[CH:21][CH:22]=3)=[CH:8][C:9]1=2

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 667890617-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

생성물 1

HCID 669366261-[4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-phenyl]-ethanone수율 62.7%

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

To 3 ml of tetrahydrofuran/0.5 ml of distilled water, 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (80.0 mg, 0.37 mmol), 4-acetylphenyl boronic acid (71 mg, 0.55 mmol), potassium carbonate (103 mg, 0.74 mmol) and tetrakis triphenylphosphine palladium (21 mg, 0.02 mmol) were added and stirred at 80° C. for 2 hours. After completion of the reaction, the mixture was extracted ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The resulting solid was recrystallized from n-hexane and diethyl ether to obtain 1-[4-(2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)-phenyl]-ethanone as yellow solid (59 mg, 62%).

후처리

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted ethyl acetate
  3. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting solid was recrystallized from n-hexane and diethyl ether

출처 및 근거

ORD 기록
ord-ceb4452679e34755b7a1d558a2344c34
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

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