Dimethylformamide → 4-chloro-6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-(nitrophenyl)quinoline

HRID 341823Notes

Reaction equation

HRID 341823 reaction equation
CN(C)C=O.[CH2:6]([C:8]1[NH:9][C:10]2[C:11]([N:18]=1)=[N:12][C:13]([CH3:17])=[CH:14][C:15]=2[CH3:16])[CH3:7].[H-].[Na+].[Cl:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32]Br)[CH:30]=2)[N:25]=[C:24]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])[CH:23]=1>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[Cl:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][N:18]3[C:11]4=[N:12][C:13]([CH3:17])=[CH:14][C:15]([CH3:16])=[C:10]4[N:9]=[C:8]3[CH2:6][CH3:7])[CH:30]=2)[N:25]=[C:24]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])[CH:23]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 153843994-Chloro-6-(bromomethyl)-2-(2-nitrophenyl)quinoline

Product 1

HCID 153844004-chloro-6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-(nitrophenyl)quinolineYield 42.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 61 ml of N,N-dimethylformamide (DMF) containing 7.45 g (42.5 mmol) of 2-ethyl-5,7-dimethyl-1H-imidazo[4,5-b]pyridine, 1.79 g (44.6 mmol) of sodium hydride (60%) was added and stirred at room temperature for 30 minutes. To the thus-prepared mixture, 15.3 g of 4-chloro-6-(bromomethyl)-2-(2-nitrophenyl)quinoline was added and stirred at room temperature for 12 hours. After adding 120 ml of toluene thereto, the thus-prepared mixture was poured into a mixture of 60 ml of toluene with 300 ml of water. After adding 120 ml of ethyl acetate thereto, the mixture was separated out and the resulting aqueous layer was extracted with a mixture of 90 ml of toluene with 90 ml of ethyl acetate. The resulting organic layers were combined and evaporated to 117.82 g in an evaporator. Then, 90 ml of toluene was added thereto and the thus-prepared mixture was washed with 90 ml of water twice. The resulting insolubles were filtered off and the organic layer was concentrated to 58.3 g in an evaporator. After allowing to stand at 5° C., the crystals precipitated were collected, washed with 10 ml of toluene twice and dried to obtain 8.12 g of 4-chloro-6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-(nitrophenyl)quinoline.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 12 hours
  3. customthe mixture was separated out
  4. extractionthe resulting aqueous layer was extracted with a mixture of 90 ml of toluene with 90 ml of ethyl acetate
  5. customevaporated to 117.82 g in an evaporator
  6. additionThen, 90 ml of toluene was added
  7. washthe thus-prepared mixture was washed with 90 ml of water twice
  8. filtrationThe resulting insolubles were filtered off
  9. concentrationthe organic layer was concentrated to 58.3 g in an evaporator
  10. customto stand at 5° C.
  11. customthe crystals precipitated
  12. customwere collected
  13. washwashed with 10 ml of toluene twice
  14. customdried

Sources & evidence

ORD record
ord-2f4d108d8cf344c686549b6e3627baa7
Source dataset
uspto-grants-1999_01
Patent number
US05856337

Reaction notes

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