Sodium hydride → 2-[5-(2-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-5-iodo-pyridine

HRID 1500346Notes

Reaction equation

HRID 1500346 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:14]=[N:13][N:12]([CH3:15])[C:11]=1[CH2:16][OH:17].Cl[C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][N:20]=1>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:14]=[N:13][N:12]([CH3:15])[C:11]=1[CH2:16][O:17][C:19]1[CH:24]=[CH:23][C:22]([I:25])=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 43971762-Chloro-5-iodopyridineHCID 67498210(4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 900206532-[5-(2-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-5-iodo-pyridineYield 48.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (0.73 g, 18.1 mmol, 60% in mineral oil) in DMF (10 ml) under N2 atmosphere at 0° C. was added [5-(2-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanol (2.5 g, 12.06 mmol) and stirred for 1 h. Then 2-chloro-5-iodopyridine (3.17 g, 13.27 mmol) was added and reaction mixture was slowly warmed to room temperature and stirred for 4 h. The reaction was monitored by TLC. The reaction mixture was quenched with ice-water, extracted with ethylacetate (50 ml), washed with brine (10 ml), dried over Na2SO4 and concentrated under reduced pressure to afford crude mass (4.4 g, 88.9% mass balance). It was triturated with hexane and the solid was filtered and dried under vacuum to furnish 2-[5-(2-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-5-iodo-pyridine (2.4 g, 48.48%) as yellow solid.

Workup

  1. customreaction mixture
  2. stirringstirred for 4 h
  3. customThe reaction mixture was quenched with ice-water
  4. extractionextracted with ethylacetate (50 ml)
  5. washwashed with brine (10 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude mass (4.4 g, 88.9% mass balance)
  9. customIt was triturated with hexane
  10. filtrationthe solid was filtered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-7bc2fe8b1f9c4ad19ed7fd9433c571ef
Source dataset
uspto-grants-2015_12
Patent number
US09206160B2

Reaction notes

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