Sodium Carbonate → 4-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one

HRID 1478545노트

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HRID 1478545 반응식
C([O-])([O-])=O.[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][N:18]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[CH:19]=2)O1.Br[C:28]1[N:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[CH:32]=[C:31]2[NH:39][O:40][CH2:41][CH3:42]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C.O.C(#N)C>[CH2:41]([O:40][NH:39][C:31]1[C:30]2[C:35](=[CH:36][CH:37]=[C:28]([C:15]3[CH:16]=[N:17][N:18]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH:19]=3)[N:29]=2)[NH:34][C:33](=[O:38])[CH:32]=1)[CH3:42]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 574162183-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridineHCID 900431286-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one

생성물 1

HCID 900440984-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one

시약·촉매·용매 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To Na2CO3 (151 mg, 1.41 mmol) was added water (1.5 ml) and acetonitrile (2 ml) and the solution was degassed for 5 min with argon. 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]pyridine (84 mg, 0.31 mmol), 6-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one (80 mg, 0.28 mmol) and Pd(dppf)Cl2 (10 mg, 0.014 mmol) were added sequentially followed by addition of acetonitrile (2 ml). The mixture was stirred at 100° C. for 15 h then allowed to cool to ambient temperature. Water and ethyl acetate were added then the phases were separated. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification by chromatography afforded of 4-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one.

후처리

  1. customthe solution was degassed for 5 min with argon
  2. temperatureto cool to ambient temperature
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography

출처 및 근거

ORD 기록
ord-f56a2a60e36e4a8c9b8b3faea3cbdef6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403845B2

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