O-Xylene → 4-bromo-1-(4-tert-butyldiphenylsilyloxymethylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)pyrrole

HRID 1586813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586813
[Br:1][C:2]1[CH:3]=[C:4]([C:32]#[N:33])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][CH:8]=2)[CH:6]=1.C[Sn]([N:38]=[N+:39]=[N-:40])(C)C.[C:41]1([CH3:48])[C:42](C)=[CH:43][CH:44]=[CH:45][CH:46]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:32]2[N:38]([C:48]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:39]=[N:40][N:33]=2)[N:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][O:14][Si:15]([C:28]([CH3:29])([CH3:30])[CH3:31])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:11][CH:12]=2)[CH:6]=1

Komponenten

4

Edukt 3

HCID 7237O-XyleneHCID 5104973Azido(trimethyl)stannaneHCID 197595594-Bromo-1-(4-tert-butyldiphenylsilyloxymethylphenyl)pyrrole-2-carbonitrile

Produkt 1

HCID 197594674-bromo-1-(4-tert-butyldiphenylsilyloxymethylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)pyrrole

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 4-bromo-1-(4-tert-butyldiphenylsilyloxymethylphenyl)pyrrole-2-carbonitrile (2.02 g) and trimethyltin azide (2.42 g) in xylene (20 ml) was stirred at 120° C. for 14 hours. After cooled to ambient temperature, the reaction mixture was concentrated in vacuo. To the residue was added trityl chloride (42 mg), triethylamine (50 μl) and methylene chloride (1 ml), and the mixture was treated in a conventional manner to give 4-bromo-1-(4-tert-butyldiphenylsilyloxymethylphenyl)-2-(1-trityl-1H-tetrazol-5-yl)pyrrole (1.63 g)

Aufarbeitung

  1. temperatureAfter cooled to ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionTo the residue was added trityl chloride (42 mg), triethylamine (50 μl) and methylene chloride (1 ml)
  4. additionthe mixture was treated in a conventional manner

Quellen und Nachweise

ORD-Eintrag
ord-8a226c2ffee545b0b9679f04133daa7b
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05215994

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