Trityl chloride → 1-(4-Methylphenyl)-4-bromo-2-cyanopyrrole
Reaction equation
C1(C(Cl)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Br:28])C1C=CC=CC=1.BrN1C(=O)CCC1=O.[CH3:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]2[CH:48]=[CH:47][CH:46]=[C:45]2[C:49]#[N:50])=[CH:40][CH:39]=1>>[CH3:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]2[CH:48]=[C:47]([Br:28])[CH:46]=[C:45]2[C:49]#[N:50])=[CH:40][CH:39]=1Participants
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-1a722f583d7f4d74ae3b6cd23edff09e
- Source dataset
- uspto-grants-1994_02
- Patent number
- US05284841
Reaction notes
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