Imidazole → HCID 58767500, compound

HRID 639907Notes

Reaction equation

HRID 639907 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]([C:27]#[N:28])[N:10]=1>COCCOC>[N:1]1([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[C:12]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:11]([C:27]#[N:28])[N:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 114264141-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile

Product 1

HCID 58767500HCID 58767500, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of imidazole (15 mg) in 2 mL DME was added NaH (12 mg, 60% dispersion in mineral oil); a precipitate formed immediately. The mixture was stirred at room temp for 5 min, then heated to 75 C. A solution of 1-chloro-4-phenyl-6-methoxyisoquinoline-3-carbonitrile (60 mg) in 1 mL DME was added via cannula. Heating continued at 75 C for 45 min. The reaction was cooled to room temp and quenched by adding a few drops of water, then partitioned between saturated aqueous sodium bicarbonate and EtOAc. The organic solution was washed with brine (1×), dried over MgSO4 and concentrated. Flash chromatography (0% to 10% MeOH (10% NH4OH) in EtOAc) gave a white solid.

Workup

  1. customa precipitate formed immediately
  2. temperatureheated to 75 C
  3. temperatureHeating
  4. waitcontinued at 75 C for 45 min
  5. temperatureThe reaction was cooled to room temp
  6. customquenched
  7. additionby adding a few drops of water
  8. custompartitioned between saturated aqueous sodium bicarbonate and EtOAc
  9. washThe organic solution was washed with brine (1×)
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated
  12. customFlash chromatography (0% to 10% MeOH (10% NH4OH) in EtOAc) gave a white solid

Sources & evidence

ORD record
ord-9b56b902e1fe4133808d897efa9bf6cd
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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