2-Nitro-1-(prop-2-ynyl)-1H-imidazole → 3-fluoro-2-(4-((2-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propan-1-ol

HRID 1011471Notes

Reaction equation

HRID 1011471 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]#[CH:11])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].[N:12]([CH:15]([CH2:18][F:19])[CH2:16][OH:17])=[N+:13]=[N-:14]>>[F:19][CH2:18][CH:15]([N:12]1[CH:11]=[C:10]([CH2:9][N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[N+:1]([O-:3])=[O:2])[N:14]=[N:13]1)[CH2:16][OH:17]

Participants

3

Reactant 2

HCID 546751432-Nitro-1-(prop-2-ynyl)-1H-imidazoleHCID 595110612-Azido-3-fluoropropan-1-ol

Product 1

HCID 595110633-fluoro-2-(4-((2-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propan-1-ol

Conditions

Temperature
60 °C

Procedure

To a vial is added alkyne 10 (1.9 g, 12.6 mmol) and 29 (1.5 g, 12.6 mmol). The solution is heated at 60° C. overnight. The material is then purified on a silica gel column using 10% MeOH:CH2Cl2 as the eluent. The material is then further purified via recrystallization using EtOAc:Hex to afford 1 as a solid.

Workup

  1. customThe material is then purified on a silica gel column
  2. customThe material is then further purified via recrystallization

Sources & evidence

ORD record
ord-61a3f4899ecf4967905b06e0d242f95b
Source dataset
uspto-grants-2011_07
Patent number
US07977361B2

Reaction notes

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