Dimethylformamide → HCID 54057074, 화합물

HRID 1585897노트

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HRID 1585897 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 54057074HCID 54057074, 화합물

시약·촉매·용매 1

HCID 11186Zinc cyanide (Zn(CN)2)촉매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4a570c90dec54eec8019776bc53ab3fe
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05939439

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