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

HRID 1478545ノート

反応式

HRID 1478545 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f56a2a60e36e4a8c9b8b3faea3cbdef6
出典データセット
uspto-grants-2016_08
特許番号
US09403845B2

反応ノート

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