Triethylamine → 5-(5-Methoxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amide

HRID 501041

Reaktionsgleichung

Reaktionsgleichung von HRID 501041
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](B(O)O)=[CH:8][C:7]=2[CH:14]=1.Br[C:16]1[CH:17]=[CH:18][C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=1.CCN(CC)CC>CCO.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[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:16]3[CH:17]=[CH:18][C:19]([C:22]([NH2:24])=[O:23])=[N:20][CH:21]=3)=[CH:8][C:7]=2[CH:14]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 7351515-Bromopyridine-2-carboxamideHCID 22221596(5-Methoxy-1-benzofuran-2-yl)boronic acid

Produkt 1

HCID 250148415-(5-Methoxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-methoxybenzofuran boronic acid (1.2 mmol), 5-bromopyridine-2-carboxamide (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 μL) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140° C. for 10 min in a microwave reactor, filtered, and the precipitate was washed with water and EtOAc and dried under vacuum to afford the title compound (75 mg). 1H NMR δ ppm 9.10 (d, 1 H) 8.34 (dd, 1 H) 8.21 (br. s., 1 H) 8.00 (d, 1 H) 7.52-7.72 (m, 3 H) 7.25 (d, 1 H) 7.00 (dd, 1 H) 3.82 (s, 3H); MS m/z 269 (M+H).

Aufarbeitung

  1. filtrationfiltered
  2. washthe precipitate was washed with water and EtOAc
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-75c556a2aa9943bda142118f08416f36
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772256B2

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