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

HRID 1943734ノート

反応式

HRID 1943734 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ceb4452679e34755b7a1d558a2344c34
出典データセット
uspto-grants-2013_03
特許番号
US08394792B2

反応ノート

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