4-Formylphenylboronic Acid → 7-[(2,4-Dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile

HRID 1178683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178683
Br[C:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:22]#[N:23])[C:10]([NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([Cl:20])=[CH:14][C:13]=3[Cl:21])=[C:5]2[S:4][CH:3]=1.[CH:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25]>COCCOC.C(=O)(O)[O-].[Na+]>[Cl:21][C:13]1[CH:14]=[C:15]([Cl:20])[C:16]([O:18][CH3:19])=[CH:17][C:12]=1[NH:11][C:10]1[C:9]([C:22]#[N:23])=[CH:8][N:7]=[C:6]2[C:2]([C:29]3[CH:30]=[CH:31][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=3)=[CH:3][S:4][C:5]=12

Komponenten

5

Edukt 2

HCID 5910734-Formylphenylboronic AcidHCID 113962683-Bromo-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile

Produkt 1

HCID 117513977-[(2,4-Dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrileAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-7-[(2,4-dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile (1.67 g, 3.89 mmol), 4-formylphenyl boronic acid (1.17 g, 7.78 mmol), and tetrakis(triphenylphosphine)pallidium (225 mg, 0.20 mmol) in 50 mL of ethylene glycol dimethyl ether and 42 mL of saturated aqueous sodium bicarbonate is heated at reflux for 2 hours and then cooled to room temperature. The precipitate is collected by filtration washing with ethyl acetate and diethyl ether to provide 1.09 g of 7-[(2,4-dichloro-5-methoxyphenyl)amino]-3-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile as a tan solid, mp 268° C. dec; 1H NMR (DMSO-d6) δ 3.87 (s, 3H), 7.44 (s, 1H), 7.79 (s, 1H), 8.01 (d, J=8 Hz, 2H), 8.23 (d, J=8 Hz, 2H), 8.55 (s, 1H), 8.73 (s, 1H), 9.86 (s, 1H), 10.05 (s, 1H); MS 454.0, 456.0 (M+H)+; HRMS found: 454.01716 (M+H)+.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe precipitate is collected by filtration
  4. washwashing with ethyl acetate and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-159712cdce714ebca497416ad1ce0474
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276519B2

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