Pyridine → N-[2-(5-formyl-2,4-dimethoxyphenylethynyl)phenyl]acetamide

HRID 347384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347384
N1C=CC=CC=1.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]#[C:15][C:16]1[C:17]([O:26][CH3:27])=[CH:18][C:19]([O:24][CH3:25])=[C:20]([CH:23]=1)[CH:21]=[O:22].[C:28](Cl)(=[O:30])[CH3:29]>C(Cl)Cl>[CH:21]([C:20]1[C:19]([O:24][CH3:25])=[CH:18][C:17]([O:26][CH3:27])=[C:16]([C:15]#[C:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:28](=[O:30])[CH3:29])[CH:23]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 161156205-(2-Aminophenylethynyl)-2,4-dimethoxybenzaldehyde

Produkt 1

HCID 11438686N-[2-(5-formyl-2,4-dimethoxyphenylethynyl)phenyl]acetamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Pyridine (453 μL, 5.61 mmol) was added to a suspension of 5-(2-amino-phenylethynyl)-2,4-dimethoxybenzaldehyde (Ex-35C, 750 mg, 2.67 mmol) in anhydrous methylene chloride (20 mL) and chilled to 0° C. The reaction mixture was treated dropwise with acetyl chloride (9.25 mL, 75.1 mmol). Upon completion the reaction was quenched with IN HCl (10 mL) and the layers were separated. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to dryness. The crude solid was purified by silica gel chromatography (5% MeOH/CH2Cl2) to yield 671 mg (78%) of N-[2-(5-formyl-2,4-dimethoxyphenylethynyl)phenyl]acetamide as an off-white solid. 1H-NMR (300 MHz, DMSO-d6) 10.15 (s, 1H), 9.23 (br s, 1H), 7.82 (m, 2H), 7.80 (s, 1H), 7.50 (dd, 1H, J=0.9, 7.8 Hz), 7.35 (dt, 1H, J=1.8, 9.3 Hz), 7.12 (t, 1H, J=7.8 Hz), 6.82 (s, 1H), 4.00 (s, 3.99 (s, 3H), 2.10 (s, 3H).

Aufarbeitung

  1. customUpon completion the reaction was quenched with IN HCl (10 mL)
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude solid was purified by silica gel chromatography (5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-0e4caf59ded94fb8a9dc64cd51b6b2ef
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173129B2

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