Water → 4-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile

HRID 1919673ノート

反応式

HRID 1919673 の反応式
CO[C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1Br)=[O:4].Cl.[NH2:12][C:13]1[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.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]>[O:4]=[C:3]1[C:5]2[S:6][CH:7]=[CH:8][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([C:19]#[N:20])=[CH:18][C:13]=2[NH:12]1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2740074Methyl 3-bromothiophene-2-carboxylateHCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

生成物 1

HCID 575006864-Oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

実験手順

Methyl-3-bromothiophene carboxylate (1.0 eq, 2.42 g, 10.95 mmol), 2-amino-4-cyanophenylboronic acid hydrochloride (1.05 eq, 2.28 g, 11.49 mmol) and cesium carbonate (2.0 eq, 7.13 g, 21.9 mmol) were suspended in dioxane (25 ml) containing 5% water. The mixture was degassed by bubbling nitrogen for 10 minutes. PdCl2(dppf) (0.05 eq, 400 mg, 0.55 mmol) was added and the mixture was stirred at reflux for 1.5 hours. The mixture was cooled down, the solid filtered, washed with dioxane, water and methanol. After drying in vacuo, 4-oxo-4,5-dihydrothieno[2,3-c]quinoline-7-carbonitrile was isolated as a solid (1.81 g, 73% yield). LCMS (ES) m/z 227 [M+1]+.

後処理

  1. customThe mixture was degassed
  2. customby bubbling nitrogen for 10 minutes
  3. temperatureat reflux for 1.5 hours
  4. temperatureThe mixture was cooled down
  5. filtrationthe solid filtered
  6. washwashed with dioxane, water and methanol
  7. customAfter drying in vacuo

出典と根拠

ORDレコード
ord-bb101d80efe34071a394b2d19a9673fe
出典データセット
uspto-grants-2012_05
特許番号
US08168651B2

反応ノート

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