Sodium hydride → 7-[2-(2,2,2-Trifluoro-ethyl)-2h-tetrazol-5-yl]-imidazo[1,2-a]pyridine

HRID 341215Notes

Reaction equation

HRID 341215 reaction equation
[H-].[Na+].[N:3]1[NH:4][N:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]2[CH:14]=[CH:15][N:16]=[C:10]2[CH:9]=1.[F:17][C:18]([F:29])([F:28])[CH2:19]OS(C(F)(F)F)(=O)=O.C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[F:17][C:18]([F:29])([F:28])[CH2:19][N:5]1[N:4]=[N:3][C:7]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[CH:15][N:16]=[C:10]3[CH:9]=2)=[N:6]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 592777617-(2H-Tetrazol-5-yl)-imidazo[1,2-a]pyridine

Product 1

HCID 593211627-[2-(2,2,2-Trifluoro-ethyl)-2h-tetrazol-5-yl]-imidazo[1,2-a]pyridineYield 39.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60 mg, 1.5 mmol) was added to a stirred suspension of 7-(2H-tetrazol-5-yl)-imidazo[1,2-a]pyridine (250 mg, 1.3 mmol) in dry DMF (4 ml) under a nitrogen atmosphere. After 1 h, Trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (1.16 g, 5 mmol) was added, followed by 18-crown-6 (260 mg, Immol). The reaction mixture was stirred at room temperature for 18 h then quenched with water and extracted with EtOAc (×2). The combined organic extracts were washed with brine (×1), dried (Na2SO4), filtered and the solvent removed in vacuo. Purification via silica column chromatography (0-2% 2M NH3MeOH/CH2Cl2) afforded the product (138 mg). MS: [M+H]+ 269.

Workup

  1. customthen quenched with water
  2. extractionextracted with EtOAc (×2)
  3. washThe combined organic extracts were washed with brine (×1)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customPurification via silica column chromatography (0-2% 2M NH3MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-712f7928c90a44bbbb01a343c0ee2eef
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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