Trimethylsilyldiazomethane → 6-bromo-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester

HRID 2102396Notes

Reaction equation

HRID 2102396 reaction equation
[Br:1][C:2]1[C:3]([F:15])=[C:4]2[N:13]=[CH:12][N:11]([CH3:14])[C:5]2=[N:6][C:7]=1[C:8]([OH:10])=[O:9].[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1COCC1.CO>[CH3:17][O:9][C:8]([C:7]1[N:6]=[C:5]2[N:11]([CH3:14])[CH:12]=[N:13][C:4]2=[C:3]([F:15])[C:2]=1[Br:1])=[O:10]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 69003086HCID 69003086, compound

Product 1

HCID 690048876-bromo-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (1.00 equivalent) in THF-MeOH at 0° C. is added TMSCHN2 (1.30 equivalents, 2 M solution in hexanes). The resulting mixture is warmed to room temperature and stirred for 2 hours. The reaction is quenched with AcOH. The reaction mixture is diluted with EtOAc. The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product that is used directly without further purification.

Workup

  1. customThe reaction is quenched with AcOH
  2. additionThe reaction mixture is diluted with EtOAc
  3. washThe organic layer is washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-373877e876df4043b879d5cc5b15932b
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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