Potassium Carbonate → 5-Oxo-2-(5-phenyl-thiophen-2-yl)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

HRID 1817823ノート

反応式

HRID 1817823 の反応式
Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[C:8](=[O:14])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[C:15]1([C:21]2[S:25][C:24](B(O)O)=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].CCCCCC.CCOC(C)=O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:14]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[N:3]=[C:2]([C:24]3[S:25][C:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:22][CH:23]=3)[C:11]([C:12]#[N:13])=[CH:10][C:9]1=2

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 2776315(5-Phenylthiophen-2-yl)boronic acidHCID 21226206Ethyl acetate hexaneHCID 247779422-Chloro-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile2 回

生成物 1

HCID 114162475-Oxo-2-(5-phenyl-thiophen-2-yl)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile収率 46%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 2-chloro-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (300 mg, 1.46 mmol) and 5-phenyl-thiophen-2-yl-boronic acid (446 mg, 2.19 mmol) in dioxane (3 ml) under an argon atmosphere was added tetrakis(triphenylphosphine)palladium (85 mg, 0.073 mmol) and 2M aqueous K2CO3 (0.7 ml). The mixture was stirred at reflux till complete (TLC; hexane-EtOAc, 2:1) consumption of 2-chloro-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile. Then water was added and the mixture was extracted by dichloromethane. The extract was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel (CH2Cl2-Hexane, 1:1), then heated under reflux in ethyl alcohol and filtered to give the title compound (220 mg, 46%) as a dark yellow solid.

後処理

  1. extractionthe mixture was extracted by dichloromethane
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (CH2Cl2-Hexane, 1:1)
  4. temperatureheated
  5. temperatureunder reflux in ethyl alcohol
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-f9bf2a320ee44ca581c1f20e596b1a9e
出典データセット
uspto-grants-2009_10
特許番号
US07598384B2

反応ノート

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