Dimethylformamide → HCID 54057074、化合物

HRID 1585897ノート

反応式

HRID 1585897 の反応式
C(OC([N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=3)[C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.[CH3:31][N:32](C=O)C>[C-]#N.[C-]#N.[Zn+2]>[C:20]([O:19][C:17]([N:13]1[CH2:14][CH2:15][C:16]2[NH:8][CH:9]=[N:10][C:11]=2[CH:12]1[C:24]1[CH:25]=[CH:26][C:27]([C:31]#[N:32])=[CH:28][CH:29]=1)=[O:18])([CH3:21])([CH3:22])[CH3:23]

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 537517454-(4-Bromo-phenyl)-6,7-dihydro-4H-imidazo[4,5-c]pyridine-1,5-dicarboxylic acid di-tert-butyl ester

生成物 1

HCID 54057074HCID 54057074、化合物

試薬・触媒・溶媒 1

HCID 11186Zinc cyanide (Zn(CN)2)触媒

反応条件

温度
80 °C

実験手順

4-(4-Bromo-phenyl)-6,7-dihydro-4H-imidazo[4,5-c]pyridine-1,5-dicarboxylic acid di-tert-butyl ester (0.55 g, 1.14 mmol) and Zn(CN)2 (0.13 g, 1.14 mmol) were stirred in anh. DMF (10 mL) and degassed with Ar for 15 min. Tetrakis(triphenylphosphine)-palladium(0) was added to the solution and stirred at 80° C. under Ar overnight. The solution was concentrated in vacuo, partitioned between EtOAc and sat. NaHCO3 soln, washed with H2O, brine, and dried over MgSO4. Filtration, concentration, and silica gel chromatography (0-2% MeOH/CH2Cl2 with NH4OH) gave the title compound.

後処理

  1. customdegassed with Ar for 15 min
  2. additionTetrakis(triphenylphosphine)-palladium(0) was added to the solution
  3. concentrationThe solution was concentrated in vacuo
  4. custompartitioned between EtOAc and sat. NaHCO3 soln
  5. washwashed with H2O, brine
  6. dry with materialdried over MgSO4
  7. filtrationFiltration, concentration, and silica gel chromatography (0-2% MeOH/CH2Cl2 with NH4OH)

出典と根拠

ORDレコード
ord-4a570c90dec54eec8019776bc53ab3fe
出典データセット
uspto-grants-1999_08
特許番号
US05939439

反応ノート

読み込み中…