Acetic Acid → 7-Methyl-2-propyl-3-[[4-(3-cyanopyridin-4-yl)phenyl]methyl]imidazo[4,5-b]pyridine

HRID 653633Notes

Reaction equation

HRID 653633 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[CH:19]=[N:20][CH:21]=[CH:22][C:23]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1)#[N:17].CC(O)=O>CN(C=O)C.C(Cl)Cl>[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[CH:22]=[CH:21][N:20]=[CH:19][C:18]=4[C:16]#[N:17])=[CH:29][CH:28]=3)[C:9]([CH2:11][CH2:12][CH3:13])=[N:10][C:3]=12

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 150208527-Methyl-2-propyl-1H-imidazo[4,5-b]pyridineHCID 183848873-Cyano-4-(4-bromomethylphenyl)pyridine

Product 1

HCID 198893907-Methyl-2-propyl-3-[[4-(3-cyanopyridin-4-yl)phenyl]methyl]imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methyl-2-propylimidazo[4,5-b]pyridine (170 mg, 1.0 mmol) from Step B in DMF at rt was added NaH (1.0 mmol). After 20 min, 3-cyano-4-(4-bromomethylphenyl)pyridine (1 mL of a 2M solution in CH2Cl2, 2 mmol) was added and the mixture was stirred at rt for 3 h. HOAc (100 μL) was added, the excess DMF was removed in vacuo then the crude product was isolated by extraction with EtOAc from brine. Purification by flash chromatography (100% EtOAc) gave the above titled compound as a glassy solid.

Workup

  1. customthe excess DMF was removed in vacuo
  2. customthe crude product was isolated by extraction with EtOAc from brine
  3. customPurification by flash chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-a0972ad679864dadbfe6f979da6697cd
Source dataset
uspto-grants-1992_07
Patent number
US05128327

Reaction notes

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