Sodium Iodide → HCID 86711890, compound

HRID 1475196Notes

Reaction equation

HRID 1475196 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:8][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:10][N:11]=2)[N:3]=1.CN(C=O)C.[Na+].[I-].[Cl:25][C:26]1[CH:31]=[C:30]([CH2:32]Cl)[CH:29]=[CH:28][N:27]=1>O>[Cl:25][C:26]1[CH:31]=[C:30]([CH2:32][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]3[O:8][C:9]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)=[N:10][N:11]=3)=[N:5]2)[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 111265732-Chloro-4-(chloromethyl)pyridineHCID 86711889HCID 86711889, compound

Product 1

HCID 86711890HCID 86711890, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(5-methyl-1H-1,2,4-triazol-3-yl)-5-phenyl-1,3,4-oxadiazole (1.00 mg, 0.44 mmol) in DMF (3 mL) Cs2CO3 (430 mg, 1.32 mmol), NaI (78 mg, 0.52 mmol) and 2-chloro-4-(chloromethyl)pyridine (78 mg, 0.48 mmol) were added. The reaction was allowed to stir overnight at RT and then diluted with H2O (10 mL), extracted with EtOAc (3×10 mL), 4:1 CHCl3:i-PrOH (5×10 mL), dried with MgSO4 and concentrated. The crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12% to 100% EtOAc) to afford 2-(1-((2-chloropyridin-4-yl)methyl)-5-methyl-1H-1,2,4-triazol-3-yl)-5-phenyl-1,3,4-oxadiazole (88 mg, 57%) as an off-white powder. MS (ES+) C17H13ClN6O requires: 352 found: 353 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×10 mL), 4:1 CHCl3
  2. dry with materiali-PrOH (5×10 mL), dried with MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12% to 100% EtOAc)

Sources & evidence

ORD record
ord-8cf2e37f8b2e4cb9810b5c55d62f99ec
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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