Tetrahydrofuran → HCID 66936733, 화합물

HRID 1943740노트

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HRID 1943740 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.CC1(C)C(C)(C)OB([C:25]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:26]=2[CH:27]=[CH:28][NH:29]3)O1.C(=O)([O-])[O-].[K+].[K+]>O>[NH:29]1[C:30]2[C:26](=[C:25]([C:7]3[CH:16]=[N:15][C:10]4[O:11][CH2:12][CH2:13][NH:14][C:9]=4[CH:8]=3)[CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:28]1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 667890617-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

생성물 1

HCID 66936733HCID 66936733, 화합물수율 139.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To 3 ml of tetrahydrofuran (THF)/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-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolane-2-yl)-1H-indole (109 mg, 0.45 mmol), potassium carbonate (103 mg, 0.74 mmol) and tetrakis triphenylphosphine palladium (172 mg, 0.15 mmol) were added and stirred at 80° C. for 4 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, and the combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane:methanol=40:1. The fractions containing the product were collected and evaporated to obtain 7-(1H-indol-4-yl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine as white solid (130 mg).

후처리

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with 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 residue was purified by column chromatography on amine silica eluting with a solvent of dichloromethane
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

출처 및 근거

ORD 기록
ord-05a591a6f3ba4285915111af68f57a83
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

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