Potassium Phosphate, Tribasic → 2-(4-cyclopropylpyridin-3-yl)-3,4-dihydrobenzo[4,5]thieno[3,2-c]pyridin-1(2H)-one

HRID 1844039

Reaktionsgleichung

Reaktionsgleichung von HRID 1844039
[C:1]1(=[O:14])[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[S:9][C:5]=2[CH2:4][CH2:3][NH:2]1.[CH:15]1([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2I)[CH2:17][CH2:16]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:15]1([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N:2]2[CH2:3][CH2:4][C:5]3[S:9][C:8]4[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=4[C:6]=3[C:1]2=[O:14])[CH2:17][CH2:16]1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 200749053,4-Dihydro-[1]benzothieno[3,2-c]pyridin-1(2H)-oneHCID 668018874-Cyclopropyl-3-iodopyridine

Produkt 1

HCID 569411282-(4-cyclopropylpyridin-3-yl)-3,4-dihydrobenzo[4,5]thieno[3,2-c]pyridin-1(2H)-oneAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3,4-Dihydro-2H-benzo[4,5]thieno[3,2-c]pyridin-1-one (I-9d: 100 mg, 0.491 mmol) was reacted with 4-cyclopropyl-3-iodo-pyridine (I-73c: 133 mg, 0.65 mmol), 1,4-dioxane (3 mL), copper iodide (9.31 mg, 0.049 mmol), trans-N,N′-dimethyl-cyclohexyl-1,2-diamine (6.9 mg, 0.049 mmol) and potassium phosphate (313.3 mg, 1.47 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 46.8 mg of the product (29.8% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-26eafa15bb9642e2b2d6b8584e44e57b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946260B2

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