Sodium hydride → HCID 19889378, compound

HRID 653647Notes

Reaction equation

HRID 653647 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:3]=12.[H-].[Na+].[C:16]([C:18]1[C:23]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=2)=[CH:22][CH:21]=[CH:20][N:19]=1)#[N:17].[NH4+].[Cl-]>CN(C=O)C.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:30][C:27]3[CH:26]=[CH:25][C:24]([C:23]4[C:18]([C:16]#[N:17])=[N:19][CH:20]=[CH:21][CH:22]=4)=[CH:29][CH:28]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridineHCID 183845142-Cyano-3-(4-bromomethylphenyl)pyridine

Product 1

HCID 19889378HCID 19889378, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 7-Methyl-2-propylimidazo[4,5-b]pyridine (320 mg, 1.83 mmol) from Example 1 Step B in DMF (9 mL) at rt was added NaH (82 mg of an 80% dispersion in oil, 2.74 mmol). After 20 min., 2-cyano-3-(4-bromomethyl- phenyl)pyridine (600 mg, 2.19 mmol) was added and the mixture was stirred at rt for 3 h. Brine (100 mL) and aqueous NH4Cl (40 mL) were added and the product was extracted with EtOAc. Purification by flash chromatography (100% EtOAc) gave the above titled compound.

Workup

  1. extractionthe product was extracted with EtOAc
  2. customPurification by flash chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-c5bc176ab3a841f380777d9dd63d30b7
Source dataset
uspto-grants-1992_07
Patent number
US05128327

Reaction notes

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