1-(4-Methylphenyl)pyrrole-2-carbonitrile → HCID 178426224, compound

HRID 1975047Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]#[N:14])=[CH:4][CH:3]=1.C([Sn]([N:28]=[N+:29]=[N-:30])(CCCC)CCCC)CCC>>[NH:28]1[C:13]([C:9]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)[CH:12]=[CH:11][CH:10]=2)=[N:14][N:30]=[N:29]1

Participants

Reactant 2

HCID 27977151-(4-Methylphenyl)pyrrole-2-carbonitrile

HCID 4984872Tributyltin azide

Product 1

HCID 178426224HCID 178426224, compound

Procedure

4-(2-(2H-2-trityltetrazol-5-yl)-1-pyrrolyl)-benzyl bromide is prepared as described in EP 0 480 204 A1 preparation 1 and 8, and as described in EXAMPLE 10. To this end 1-(4-methylphenyl)-2-cyanopyrrole is reacted with tributyltin azide to give 4-(2-(1H-tetrazol-5-yl)-1-pyrrolyl)-methylbenzene, which is protected by reaction with triphenylmethyl chloride. The benzylic methyl group of (2-(2H-2-trityltetrazol-5-yl)-1-pyrrolyl)-methylbenzene is then converted to the benzyl bromide with N-bromosuccinimide. An analog with a bromo substituent in the pyrrole ring is prepared from the same starting material 1-(4-methylphenyl)-2-cyanopyrrole by reaction with N-bromosuccinimide at room temperature to give 1-(4-methylphenyl)-4-bromo-2-cyanopyrrole. This is further reacted by analogy to the unsubstituted compound.

Sources & evidence

ORD record: ord-edd0d1b187b94be9954c0c7a754f5512
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284841

Reaction notes

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