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

HRID 369837노트

반응식

HRID 369837 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-70f44494bccb4509b17d65f6096f4c41
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140332

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