8-Ethynyl-1,4-dioxaspiro[4.5]decan-8-ol → 8-(6-Methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1354211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354211
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.[C:21]([C:23]1([OH:33])[CH2:32][CH2:31][C:26]2([O:30][CH2:29][CH2:28][O:27]2)[CH2:25][CH2:24]1)#[CH:22]>CN(C=O)C.C(N(CC)CC)C.O.CCOCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:22]#[C:21][C:23]1([OH:33])[CH2:32][CH2:31][C:26]2([O:27][CH2:28][CH2:29][O:30]2)[CH2:25][CH2:24]1

Komponenten

9

Edukt 2

HCID 111059858-Ethynyl-1,4-dioxaspiro[4.5]decan-8-olHCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate

Produkt 1

HCID 211046678-(6-Methoxy-[1,5]naphthyridin-4-ylethynyl)-1,4-dioxa-spiro[4.5]decan-8-ol

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A degassed solution of trifluoromethanesulphonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (986 mg, 3.2 mmol) (WO 03 010138) and 8-ethynyl-1,4-dioxa-spiro[4.5]decan-8-ol (638 mg, 3.5 mmol) (prepared according to J. Chem. Soc. Perk. Trans. 1, 2000, 3382) in DMF (3 ml) was added dropwise to a likewise degassed suspension of copper(I) iodide (50 mg) and PdCl2(PPh3)2 (100 mg) in DMF (2 ml) and triethylamine (3 ml). The reaction mixture was stirred at room temperature for 30 minutes and diluted with water and ether, and the organic phase was washed with water, saturated ammonium chloride solution and saturated sodium chloride solution, dried over MgSO4 and concentrated. The crude product was purified by chromatography on silica gel (hex/EtOAc 1:1, EtOAc).

Aufarbeitung

  1. washthe organic phase was washed with water, saturated ammonium chloride solution and saturated sodium chloride solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography on silica gel (hex/EtOAc 1:1, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-3e4cb1a0340c4ed8a97239c3925cc9cb
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223776B2

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