Triethylamine → HCID 59321081, compound

HRID 341206Notes

Reaction equation

HRID 341206 reaction equation
[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11](O)[CH2:12][N+:13]([O-:15])=[O:14])=[CH:10][C:5]2=[N:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[I:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9](/[CH:11]=[CH:12]/[N+:13]([O-:15])=[O:14])=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59320904HCID 59320904, compound

Product 1

HCID 59321081HCID 59321081, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-Iodo-imidazo[1,2-a]pyridin-7-yl)-2-nitro-ethanol (116 mg, 0.35 mmol) in CH2Cl2 (2 ml) at 0° C. was added triethylamine (121 μl, 0.87 mmol) and methanesulfonyl chloride (38 μl, 0.49 mmol). The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1 h. The mixture was partitioned between CH2Cl2 and H2O, the organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by silica column chromatography (0-50% MeOH in Et2O) to afford the product (57 mg). MS: [M+H]+=316.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and H2O
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by silica column chromatography (0-50% MeOH in Et2O)

Sources & evidence

ORD record
ord-86119c51ceeb42029cfeb76df39060fa
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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