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

HRID 1586813Notes

Reaction equation

HRID 1586813 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
120 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-8a226c2ffee545b0b9679f04133daa7b
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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