Triethylamine → 5-(1-Benzyl-5-iodo-1h-1,2,3-triazol-4-yl)-2-fluorobenzonitrile

HRID 1752552Notes

Reaction equation

HRID 1752552 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[C:8]#[N:9])#[CH:2].[CH2:12]([N:19]=[N+:20]=[N-:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[I:29]Cl>[Cu]I.O1CCCC1>[CH2:12]([N:19]1[C:2]([I:29])=[C:1]([C:3]2[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=2)[C:8]#[N:9])[N:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12152Benzyl azideHCID 24640Iodine chlorideHCID 534292955-Ethynyl-2-fluorobenzonitrile

Product 1

HCID 687372695-(1-Benzyl-5-iodo-1h-1,2,3-triazol-4-yl)-2-fluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 62B (200 mg, 1.38 mmol), benzyl azide (0.176 mL, 1.38 mmol), tetrahydrofuran (12 mL), triethylamine (0.230, 1.56 mmol), CuI (263 mg, 1.38 mmol) and ICl (0.069 mL, 1.38 mmol) under argon was stirred at room temperature for 24 hours. The solvent was evaporated and the crude mixture was dissolved in dichloromethane, loaded directly onto a silica gel column and eluted with ethyl acetate/hexanes (10-20%) to afford the title compound. MS (ESI+) m/z 404.9 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was dissolved in dichloromethane
  3. washeluted with ethyl acetate/hexanes (10-20%)

Sources & evidence

ORD record
ord-b9eaf400ba7a44cb8522ffeb28a06fd0
Source dataset
uspto-grants-2015_10
Patent number
US09163007B2

Reaction notes

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