Phosphorus trichloride → 4-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60249
[Cl:1][C:2]1[C:10]2[C:9]3[CH:11]=[C:12]([C:16]#[N:17])[N+:13]([O-])=[CH:14][C:8]=3[N:7]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=2[N:5]=[CH:4][CH:3]=1.P(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:10]2[C:9]3[CH:11]=[C:12]([C:16]#[N:17])[N:13]=[CH:14][C:8]=3[N:7]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=2[N:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 24387Phosphorus trichlorideHCID 670274914-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile-7-oxide

Produkt 1

HCID 582666684-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrileAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile-7-oxide (1.3 g, 3.52 mmol) in dichloromethane (11 mL) was treated with phosphorus trichloride (2N solution in dichloromethane, 1.9 mL, 3.9 mmol) and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 40 g, ISCO, 0-40% ethyl acetate in heptane) to afford the title compound as a white solid (1.2 g, 93%). 1H NMR (400 MHz, CDCl3) δ 9.20 (d, J=0.9, 1H), 8.74 (d, J=0.9, 1H), 8.60 (d, J=5.3, 1H), 7.39 (d, J=5.3, 1H), 6.02 (s, 2H), 3.60 (t, J=8.0, 2H), 0.94 (t, J=8.0, 2H), −0.08 (s, 9H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography (silica, 40 g, ISCO, 0-40% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-a4019a121dcc4270aed67ba750ef0c7a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440976B2

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