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

HRID 369837ノート

反応式

HRID 369837 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-70f44494bccb4509b17d65f6096f4c41
出典データセット
uspto-grants-2000_10
特許番号
US06140332

反応ノート

読み込み中…