Triethylamine → Methyl 2-methoxy-4-(phenylethynyl)nicotinate

HRID 1034936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034936
I[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH3:13])[N:5]=[CH:4][CH:3]=1.[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)#[CH:15].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>O.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.[Cu]I>[CH3:13][O:12][C:6]1[N:5]=[CH:4][CH:3]=[C:2]([C:15]#[C:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11430Potassium CarbonateHCID 58819970Methyl 4-iodo-2-methoxynicotinate

Produkt 1

HCID 58093657Methyl 2-methoxy-4-(phenylethynyl)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-iodo-2-methoxynicotinate (400 mg, 1.36 mmol), ethynylbenzene (167 mg, 1.63 mmol), Pd(PPh3)2Cl2 (47 mg, 0.068 mmol), CuI (7.7 mg, 0.04 mmol) and triethylamine (400 uL) is stirred at room temperature for 20 hours. The mixture is diluted with water, made alkaline with K2CO3 and extracted with CHCl3. The organic layer is washed with brine, water and concentrated under vacuum. The title compound is purified by silica gel column chromatography using hexane/ethyl acetate as eluent. MS m/z 268.1 (M+1).

Aufarbeitung

  1. extractionextracted with CHCl3
  2. washThe organic layer is washed with brine, water
  3. concentrationconcentrated under vacuum
  4. customThe title compound is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7cb4d83a9beb4015a4ac07bb86425a80
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546370B2

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