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Bis(pyridine)iodonium tetrafluoroborate → 3-Iodo-6-methoxy-7-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-yl)-furo[3,2-b]pyridine

HRID 1258435
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Reaktionsgleichung

Reaktionsgleichung von HRID 1258435
C[O:2][C:3]1[C:4]([C:21]#[C:22][C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)=[N:5][CH:6]=[C:7]([O:19][CH3:20])[C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.F[B-](F)(F)F.[IH2+:34].N1C=CC=CC=1.N1C=CC=CC=1>C1COCC1>[I:34][C:21]1[C:4]2=[N:5][CH:6]=[C:7]([O:19][CH3:20])[C:8]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:3]2[O:2][C:22]=1[C:23]1[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=1
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Komponenten

4

Edukt 2

HCID 10883201Bis(pyridine)iodonium tetrafluoroborateHCID 686980513,5-dimethoxy-4-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-ylethynyl)pyridine

Produkt 1

HCID 686957033-Iodo-6-methoxy-7-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-yl)-furo[3,2-b]pyridineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3,5-dimethoxy-4-(4-methoxy-benzyloxy)-2-(1-methyl-1H-pyrazol-4-ylethynyl)pyridine (80 mg, 0.21 mmol) in dry THF (2 ml) was added bispyridine iodonium tetrafluoroborate (94 mg, 0.25 mmol) and the reaction was refluxed for 0.5 hours. After cooling, the reaction was quenched with 10% Na2S2O3 (aq) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated onto silica-gel under reduced pressure. The solid residue was purified by flash chromatography (silica-gel, eluted with EtOAc:hexanes, 3:2) to give the product as a white solid (65 mg, 63%). 1H—NMR (300 MHz, CDCl3) δ 8.23 (s, 1H), 8.16 (s, 1H), 8.15 (s, 1H), 7.38 (d, J=8.6 Hz, 2H), 6.86 (d, J=8.6 Hz, 2H), 5.60 (s, 2H), 3.99 (s, 3H), 3.93 (s, 3H), 3.77 (s, 3H).

Aufarbeitung

  1. temperaturethe reaction was refluxed for 0.5 hours
  2. temperatureAfter cooling
  3. customthe reaction was quenched with 10% Na2S2O3 (aq)
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated onto silica-gel under reduced pressure
  8. customThe solid residue was purified by flash chromatography (silica-gel, eluted with EtOAc:hexanes, 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-ce1bd6a0577345fbb1cab9257ccf837f
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466163B2

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