2,6-Lutidine → 2-(5-Amino-4-cyano-3-methyl-1H-pyrrol-2-yl)-N-benzyl-pyridinium bromide

HRID 369837Notes

Reaction equation

HRID 369837 reaction equation
[Br-].[CH2:2]([N+:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Br:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:16][C:17]1[NH:18][CH:19]=[C:20]([CH3:24])[C:21]=1[C:22]#[N:23].N1C(C)=CC=CC=1C>C(Cl)Cl>[Br-:15].[NH2:16][C:17]1[NH:18][C:19]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][N+:9]=2[CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[C:20]([CH3:24])[C:21]=1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 3999752-Amino-4-methyl-1H-pyrrole-3-carbonitrileHCID 12552152HCID 12552152, compound

Product 1

HCID 232827662-(5-Amino-4-cyano-3-methyl-1H-pyrrol-2-yl)-N-benzyl-pyridinium bromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, 1.81 g (5.5 mmol) of N-benzyl-2-bromo-pyridinium bromide [for preparation see J. Heterocyclic Chem. 28,1083 (1991)] are added to 605.5 mg (5.0 mmol) of 2-amino-3-cyano-4-methyl-pyrrole [for preparation see Synthesis (1976), 51] in 40 ml of methylene chloride and 639 μl (5.5 mmol) of lutidine. After 5.5 hours' stirring at RT, the reaction mixture is concentrated by evaporation to approximately half its original volume. Filtering the suspension and washing with methylene chloride/ethyl acetate (1:1) and ethyl acetate/hexane (1:1) yield the title compound; 1H-NMR (300 MHz, DMSO-d6): 10.83 (s, 1H), 9.10 (d, J=7, 1H), 8.49 (t, J=7, 1H), 7.96 (m, 2H), 7.30 (m, 3H), 6.95 (m, 2H), 6.57 and 5.80 (2s, each 2H), 1.76 (s, 3H); FAB-MS: (M+H)+ =289.

Workup

  1. concentrationthe reaction mixture is concentrated by evaporation to approximately half its original volume
  2. filtrationFiltering the suspension
  3. washwashing with methylene chloride/ethyl acetate (1:1) and ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-70f44494bccb4509b17d65f6096f4c41
Source dataset
uspto-grants-2000_10
Patent number
US06140332

Reaction notes

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