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Dimethylformamide → 1-ethyl-2-(4-fluorophenylethynyl)-6-methoxy-1H-indole-3-carbonitrile

HRID 252494
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252494
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1I)[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1.CN(C=O)C.CCN(CC)CC>O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:25]#[C:24][C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 594256441-ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile

Produkt 1

HCID 116597201-ethyl-2-(4-fluorophenylethynyl)-6-methoxy-1H-indole-3-carbonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178419050HCID 178419050, VerbindungKatalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1-ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile (150 mg, 0.46 mmol), prepared as described in example 1Ga, step A, 4-fluorophenylacetylene (80 mg, 0.0.69 mmol), bis(triphenylphosphine)palladium (II) dichloride (6 mg, 0.009 mmol) and CuI (4 mg, 0.018 mmol) is added to a sealable tube and alternately evacuated and flushed with N2. To the tube is then added DMF (4 mL) and Et3N (0.25 mL, 1.84 mmol) and the reaction is heated at 80° C. for 20 h and then cooled to room temperature. The reaction mixture is diluted with H2O and extracted with EtOAc (2×). The combined organic phases are washed with H2O (3×) and saturated NaCl and then dried over MgSO4 and concentrated. The crude reaction mix is absorbed on silica gel (0.6 g) and chromatographed over silica gel using EtOAc/hexanes (10-20%) as eluent to afford 120 mg (82%) of 1-ethyl-2-(4-fluorophenylethynyl)-6-methoxy-1H-indole-3-carbonitrile as a yellow solid.

Aufarbeitung

  1. customprepared
  2. additionis added to a sealable tube
  3. customalternately evacuated
  4. customflushed with N2
  5. extractionextracted with EtOAc (2×)
  6. washThe combined organic phases are washed with H2O (3×) and saturated NaCl
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude reaction
  10. additionmix
  11. customis absorbed on silica gel (0.6 g)
  12. customchromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9a0aea9fe0ad41cb889228b02f0dbcff
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868037B2

Notizen zur Reaktion

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