2,6-Lutidine → HCID 23282697、化合物

HRID 369831ノート

反応式

HRID 369831 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.[CH2:16]([O:18][C:19]([C:21]1[CH:25]=[CH:24][NH:23][C:22]=1[NH2:26])=[O:20])[CH3:17].N1C(C)=CC=CC=1C>C(Cl)Cl>[Br-:15].[NH2:26][C:22]1[NH:23][C:24]([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)=[CH:25][C:21]=1[C:19]([O:18][CH2:16][CH3:17])=[O:20]

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 12111022Ethyl 2-amino-1H-pyrrole-3-carboxylate2 回HCID 12552152HCID 12552152、化合物

生成物 1

HCID 23282697HCID 23282697、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Under an argon atmosphere, 658 mg (2.0 mmol) of N-benzyl-2-bromo-pyridinium bromide (for preparation see: J. Heterocyclic Chem. 28, 1083 (1991)) are introduced into 20 ml of abs. methylene chloride, and 308 mg (2.0 mmol) of 2-amino-pyrrole-3-carboxylic acid ethyl ester [for preparation see: J. Heterocyclic Chem. 23, 1555 (1986)] are added thereto. The reaction mixture is stirred for 2 days with the exclusion of light. Since the reaction is not complete, 232 μl (2 mmol) of 2,6-lutidine and a further 0.20 mmol of 2-amino-pyrrole-3-carboxylic acid ethyl ester are added. After a further 12 hours' stirring, the reaction mixture is concentrated by evaporation and the residue is digested in isopropanol. Filtering, washing with hexane and drying yield the title compound which, according to its 1H-NMR spectrum, still contains approximately 10% N-benzyl-2-bromo-pyridinium bromide; 1H-NMR (300 MHz, DMSO-d6): 11.45 (1H), 8.70 (d, J=7, 1H), 8.38 (t, J=7, 1H), 8.00 (d, J=7, 1H), 7.67 (t, J=7, 1H), 7.42 (m, 3H), 7.14 (d, J=7, 2H), 6.85 (d, J=3, 1H), 6.45 (sb, 2H), 5.91 (s, 2H), 4.13 (q, J=7, 2H), 1.19 (t, J=7, 3H); FAB-MS: (M+H)+ =322.

後処理

  1. stirringAfter a further 12 hours' stirring
  2. concentrationthe reaction mixture is concentrated by evaporation
  3. filtrationFiltering
  4. washwashing with hexane
  5. customdrying

出典と根拠

ORDレコード
ord-99c38aa063b949b2b3bbc779ac75062e
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…